DSC_0035

A woman in Portland, Maine during a long weekend coastal escape.

Portland, Maine is an underrated city in the United States that definitely deserves more recognition. Between the poetic harbors and wharfs, delicious lobster, picturesque lighthouses and the charming city, there is so much to fall in love with in Portland, Maine and that is why it makes for the best long weekend in New England.

A woman enjoying a long weekend in Portland, Maine

Not to get confused with Portland, Oregon, Portland, Maine is a completely different city on the East Coast. During May 2017, my friend and I did a mini road trip to Portland to experience all of the jewels this stunning New England city is known for.

Old Port in Portland, Maine

Below is the perfect long weekend itinerary for Portland, Maine.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

A Long Weekend Itinerary for Portland, Maine

Traveling to Portland, Maine:

Nature in Kennebunkport

The drive from the New York City area to Portland is around 6 hours. As you drive north, you will pass by Stamford, Connecticut; Hartford, Connecticut; Worcester, Massachusetts; Portsmouth, New Hampshire and a few smaller cities and towns that you could stop in, explore and grab food. 

In addition to New York City, Portland is a great city to drive to from Boston, which is only a 2.5-hour drive; Montréal, which is a 5.5-hour drive; Québec City, which is a 5-hour drive and Providence, which is a 3-hour drive. If you are planning to drive to Portland and don’t want to use the miles on your car, it is recommended that you rent one. In addition, if you aren’t from the Northeast of the United Sates or Canada, you could fly into Portland International Jetport or Portsmouth International Airport at Pease. You could find affordable flights through Skyscanner.

Looking for an RV for your next trip, reserve here!

Where to Stay in Portland, Maine during a Long Weekend:

Sunflower in Portland, Maine

When it comes to finding accommodation in Portland, Maine there are a variety of hotels and rental properties to choose from, based on budget, for your long weekend getaway.

My friend and I stayed at Portland Sheraton at Sable Oaks in South Portland. It was about a 10 minute drive to the heart of the city. (There are Ubers and Lyfts in Portland as well. When we went out, we took advantage of either one of these services.)

In addition to hotels, you could also choose from a selection of Airbnb and Vrbo options within the Portland area. Click here to check out the hotels in and around Portland. Below are my recommendations:

Luxury Accommodation: The Press Hotel, Autograph Collection

Boutique Accommodation: Portland Harbor Hotel

Mid-Budget Accommodation: The Francis

Budget Accommodation: Holiday Inn Portland

Long Weekend Itinerary for Portland, Maine:

Spring Point Ledge Light in Portland, Maine

Day 1 in Portland, Maine:

Savor Dinner on the Wharf:
A crab roll from Boone's Fish House in Portland, Maine

When my friend and I arrived in Portland, Maine for our long weekend, we couldn’t wait to start exploring! I was also excited for some fresh seafood.

Since we arrived a little later in the day, we settled into our hotel and then headed to a warm and welcoming waterfront restaurant on Portland’s famous Commercial Street called Boone’s Fish House & Oyster Room. When we arrived in Portland, it was cold and rainy, so Boone’s was a great place to warm up since they have several fireplaces and a great selection of Portland-brewed beers.

For dinner, I ate a delicious crab roll on a brioche bun and my friend had the lobster mac and cheese. All of Boone’s seafood is fresh and delivered right to the restaurant from the water.

Grab After Dinner Drinks:
Commercial Street in Portland, Maine

Our first night took us through history as we made our way around the cobblestoned streets. (Portland is such a lovely city to stroll around during a beautiful evening!) The first stop of the night was at Vena’s Fizz House, a corner-side cocktail house with a charming turn-of-the-century atmosphere.

Vena’s offers a plethora of drink options for all ages that features fresh ingredient fizz drinks that are both alcoholic and non-alcoholic along with mocktails and cocktails. The adorable bar even has a boutique that offers Vena’s mixology of syrups, infusions and other ingredients to create your own craft cocktails at home.

The best part about Vena’s is that their drinks aren’t too strong. I know everyone has his or her own drink preferences, but I cannot enjoy something when all I taste is alcohol. I ordered a Maple Syrup Switchel that consisted of rum, fresh Maine maple, molasses, ginger, coffee and aromatic bitters. I was able to savor every flavor and it was unforgettable.

After enjoying some time at Vena’s and getting to know the friendly owners, we took the party over to a local Portland bar on Commercial Street called Three Dollar Dewey’s. This dive bar is a great place to get cheap beer and meet friendly people.

Day 2 in Portland, Maine:

Enjoy Coffee and Brunch in Old Port:
Two women enjoying a long weekend getaway in Portland, Maine

Our second day during our long weekend in Portland, Maine was absolutely gorgeous! We wanted to take advantage of the sunny weather, so we headed back into Old Port (downtown Portland) to walk around and grab a freshly brewed cup of coffee at Coffee by Design on Congress Street (there are a few locations throughout the city).

After walking around the neighborhoods with our coffee and admiring all of the cute New England architecture, we were starving for a delicious breakfast.

Brunch at Little Tap House during a long weekend in Portland, Maine

Portland is known to have many great brunch spots, so we had many options to choose from. Since we were in the area, we stopped at an adorable farm-to-table gastro-pub called Little Tap House.

When we walked inside, all of the furniture pieces were rustic and the decorations were colorful and charming. I savored a delicious breakfast bowl of home fries, caramelized onion, locally sourced mushrooms, peppers and scallions topped with fried eggs with a mimosa on the side. It definitely hit the spot!

Stroll around Portland’s Promenade:
Coastal towns near Portland, Maine

Once we finished brunch, we were full, so a walk around the city was well needed. We walked down Congress Street, through a few neighborhoods, before we hit the Eastern Promenade – a breathtaking costal trail, built along an old rail corridor that offers beautiful views of the harbor and Casco Bay.

Since it was a gorgeous day, there were plenty of sailboats in the water, people were hanging out on the lawn and East End Beach and, of course, their adorable puppies were playing in the chilling water. This 2.1-mile trail allows people to bike, run, bird feed, dog walk and enjoy the day. You can even take a train ride around the promenade and learn more about this wonderful seaport city.

Overall, enjoying the Eastern Promenade is a must-do during a long weekend in Portland, Maine.

Admire the Picturesque Lighthouses:
A woman at Spring Point Ledge Light during a long weekend trip to Portland, Maine

The afternoon took us over to South Portland to see the lighthouses. Even though I have spent every summer at the Jersey Shore, I had never seen a lighthouse in real life prior to this trip. (There is one in New Jersey on Long Beach Island.) Over the years, I have seen lighthouses in Malta, Portugal, Cape May and Delaware.

The first lighthouse we saw during our long weekend in Portland, Maine was the Spring Point Ledge Light, right off the Southern Maine Community College campus. The Spring Point Ledge Light is a dangerous obstruction on the west side on the main shipping channel.

Unlike many of the lighthouses, this tower is built of brick instead of cast-iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse.

Unfortunately, on the day we went, we were unable to tour the inside of the lighthouse, but it was still cool to walk up to it and enjoy the views of the harbor, pebble beaches, historic forts and the beautiful Casco Bay. I definitely recommend wearing comfortable shoes when you walk across the breakwater because there are a lot of ways you can fall and get hurt.

Fort Williams Park in Cape Elizabeth

After our time at Spring Point Ledge Light, we drove 15 minutes into the affluent town of Cape Elizabeth to the stunning Fort Williams Park. The beautiful park features 90 acres of rugged beauty along the Casco Bay.

There are also several hiking paths with beautiful cliffside views of the water crashing onto the rocks. In addition, there are many great lookout spots, a rock beach, picnic areas, a playground, ball fields and more!

Seeing Portland Head Light during a long weekend in Portland, Maine

As you continue to walk south, you can catch a stunning view of the symbolic Portland Head Light, modeling its beauty on the coastal cliffs of Cape Elizabeth.

The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the beautiful lighthouse reminded us of why we chose to come to Maine in the first place.

Overall, Portland Head Light and Fort Williams park are absolutely breathtaking and you cannot visit Portland, Maine during a long weekend trip and not come to this spot.

Eat the Best Lobster Rolls:
Bite Into Maine in Fort Williams Park

Before visiting Maine, I read on a few travel blogs that the best lobster rolls were found in a small airstream in Fort Williams Park called Bite Into Maine.

Since the airstream is so small, we had a tough time trying to locate it, but it gave us the opportunity to explore the park more and interact with the locals. We finally found it and indulged in mouthwatering fresh Maine lobster chunks on a warm bun. There are so many types of lobster rolls for you to choose from through Bite Into Maine.

Have a Chowder Dinner in Portland:

I was recommended by a friend to check out Gilbert’s Chowder House right off the wharf on Commercial Street. During our second evening in Portland, I was in the mood for a warm soup, so I was thrilled to give this place a try!

New England Clam Chowder

I savored a delicious New England clam chowder in a freshly baked bread bowl. It was the perfect light dinner and Gilbert’s offers a warm and welcoming atmosphere.

Have a Fun Night Out in Portland:

The night took us over to Bull Feeney’s, which is a fancy Irish tavern located on Fore Street that offers something for everyone to enjoy. (New England has a heavy Irish influence.)

On the bottom floor, you can grab a drink and sit down at one of their tables and talk with friends. The second story has a dance floor with a room off to the side that hosts Maine’s best cover bands. You can even get seated service and enjoy a lovely Irish brunch or dinner.

Day 3 in Portland, Maine:

A woman enjoying a long weekend in Portland, Maine discovering coastal towns
Adventure through Southern Maine’s Beaches:
A woman at Old Orchard Beach in Southern Maine

Originally, my friend and I were supposed to do a day trip to Acadia National Park in Bar Harbor, but it was further away than we thought for a day trip. (Looks like I have to make my way back up to Maine.) However, we did end up exploring the beautiful beaches south of Portland to make up for it!

Below are beach towns to include in a long weekend itinerary for Portland, Maine.

Visiting Biddeford Pool, Maine during a long weekend getaway to Portland, Maine

Old Orchard Beach: A half hour south of Portland is Old Orchard Beach. We started our fun day there where we grabbed breakfast, wandered around the boardwalk as well as walked on the beach. (We enjoyed breakfast at Joseph’s by the Sea.)

A seaside walking trail in Biddeford Pool, Maine

Biddeford Pool: This secluded coastal town has beautiful cedar houses and a breathtaking rock beach. Even though it was Memorial Day Weekend when we traveled to Biddeford Pool, there wasn’t a soul around!

We walked around the rock beach towards the white sand beach. The cool part about these beaches is that they have a small hiking trail through the woods and meadows that you walk through to get to them. During our time there, we got to see a lot of stunning birds.

The beach at Kennebunkport

Kennebunkport: The small town of Kennebunkport is just as beautiful as Biddeford Pool, except there were more people. I loved all of the colorful trees in the beach area. It was so breathtaking! We also enjoyed walking around the downtown area and grabbing some coffee, snacks and more before heading back to Portland.

Enjoy a Fancy Dinner in Portland:

During our last evening in Portland, Maine, we wanted to get a nice dinner on the water. Since the weather was beautiful, we were able to enjoy a beautiful sunset and savor delicious lobster rolls (for one last time) at DiMillo’s on the Water. Instead of getting drinks afterwards, we ended up grabbing dessert at Gorgeous Gelato.

Day 4 in Portland:

A woman on the beach at Biddeford Pool near Portland, Maine during a long weekend
Savor Donuts for Breakfast:

It was raining pretty hard during our last morning in Portland, so we wanted to get on the road early. We first stopped at The Holy Donut located in Old Port before hitting the road. Their donuts are delicious and made with locally grown potatoes. It was tasty, unique and the perfect way to end our time in Portland.

Click here to discover more to do in Portland, Maine during a long weekend.


A woman at Biddeford Pool during a long weekend in Portland, Maine

I hope you all enjoyed reading about my long weekend getaway itinerary for Portland, Maine. If you have any questions about my time in Portland, please email me at [email protected]

Make sure to pin this post if you find it useful!

A long weekend itinerary for Portland, Maine

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., ME State Capital: Augusta, Time Zone: Eastern Standard Time

Click here to join my private blog sharing Facebook group.

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Portland, Maine Look:

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22 Comments

  1. Merrie Rodriguez on August 15, 2019 at 11:43 pm

    This is my husbands DREAM vacation!! We are hoping to get there ASAP lol!

    • Taylor Deer on August 16, 2019 at 9:17 am

      Portland is so beautiful, you guys would love it so much! If you have the time too, I recommend visiting Acadia National Park too.:)

  2. Anna on August 16, 2019 at 11:59 am

    It sounds like a wonderful way how to spend a long weekend ♥!
    And Donuts for breakfast – seriously?? That must be soo amazing :D!!!

    • Taylor Deer on August 16, 2019 at 12:38 pm

      Yes, it was quite lovely and Maine is so peaceful! lol yes, I need to do better about not having donuts for breakfast, but they are amazing! 🙂

  3. Aswani on August 16, 2019 at 2:25 pm

    Didn’t realize there is a Portland in Maine! Gorgeous picture Taylor. Makes me want to visit this place!

    • Taylor Deer on August 17, 2019 at 5:18 pm

      Yes, it’s so beautiful and the seafood is amazing! You definitely have to go at some point.

  4. Amanda on July 28, 2020 at 10:56 am

    I’m wondering where you saw that pretty white building? Which beach and how did you get there? Thank you!

    • Taylor Deer on July 28, 2020 at 11:03 am

      Hi Amanada, If you’re referring to the white hotel on the beach, that was in Biddeford Pool, Maine. Overall, Biddeford isn’t a big town and it’s very quiet. You could easily walk around the beach and find it, that is what we did. We mainly walked around the East Point Sanctuary. Honestly, I don’t know the name of the hotel and I even tried looking it up and couldn’t find it. I visited in 2017, so it possibly may not even be there anymore. I couldn’t tell if it was abandoned when I was there.

  5. Cosette on June 3, 2021 at 6:25 am

    Such a beautiful area of the USA. I haven’t been to this part yet, but it looks so beautiful. The food also looks delicious.

    • Taylor Deer on June 3, 2021 at 9:30 am

      New England truly is beautiful and I love all of the seafood there. 🙂

  6. Puloma Banerjee on June 12, 2021 at 12:24 pm

    Wow such an amazing post on Portland, Maine. The scenic beaches and landscape is tempting and so is the seafood! Makes me want to visit it!

    • Taylor Deer on June 12, 2021 at 8:33 pm

      Thank you so much Puloma! It really is such a beautiful part of the country. 🙂

  7. Monica on June 12, 2021 at 10:31 pm

    Maine is just so beautiful in the photos. I would love to know more about campgrounds in the state.

    • Taylor Deer on June 13, 2021 at 11:08 am

      It really is such a beautiful state. I don’t know much about camping there, but I can imagine it is wonderful! 🙂

  8. Brianna on June 12, 2021 at 10:41 pm

    I loved Portland and especially Vena’s Fizz House! Looks like you had perfect weather too.

    • Taylor Deer on June 13, 2021 at 11:09 am

      Yes, it is such a cute spot! I’d love to go back. I went during Memorial Day Weekend in 2017 and it was quite chilly, but we were lucky with no rain. 🙂

  9. Vanessa on June 13, 2021 at 8:15 am

    Looks like you did all the quintessential things when visiting Maine! I pinned this post as I’ve always wanted to visit the state. Oh, those lobster rolls and a bowl of clam chowder are calling my name.

    • Taylor Deer on June 13, 2021 at 11:10 am

      The seafood there is some of the best in the world! You would love Portland Vanessa. 🙂

  10. Linda (LD Holland) on June 13, 2021 at 3:24 pm

    We spent a week on the coast but only got a few hours in Portland. But we did find some great seafood for lunch one day! I can see that next time we need to spend some more time there. A great base to see the lighthouses along the bay.

    • Taylor Deer on June 14, 2021 at 4:46 pm

      Yes, it is such a nice city! I loved all the seafood there. 🙂

  11. Emilia Taneva on June 13, 2021 at 5:32 pm

    I love Portland! One of my best friends live there but I haven’t been in years. Your trip and photos look so fun!

    • Taylor Deer on June 14, 2021 at 4:49 pm

      It is such a great city! 🙂 Thank you!

Leave a Comment





DSC_0035

A woman in Portland, Maine during a long weekend coastal escape.

Portland, Maine is an underrated city in the United States that definitely deserves more recognition. Between the poetic harbors and wharfs, delicious lobster, picturesque lighthouses and the charming city, there is so much to fall in love with in Portland, Maine and that is why it makes for the best long weekend in New England.

A woman enjoying a long weekend in Portland, Maine

Not to get confused with Portland, Oregon, Portland, Maine is a completely different city on the East Coast. During May 2017, my friend and I did a mini road trip to Portland to experience all of the jewels this stunning New England city is known for.

Old Port in Portland, Maine

Below is the perfect long weekend itinerary for Portland, Maine.

**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like.


Pin the Below Image to Keep Handy

A Long Weekend Itinerary for Portland, Maine

Traveling to Portland, Maine:

Nature in Kennebunkport

The drive from the New York City area to Portland is around 6 hours. As you drive north, you will pass by Stamford, Connecticut; Hartford, Connecticut; Worcester, Massachusetts; Portsmouth, New Hampshire and a few smaller cities and towns that you could stop in, explore and grab food. 

In addition to New York City, Portland is a great city to drive to from Boston, which is only a 2.5-hour drive; Montréal, which is a 5.5-hour drive; Québec City, which is a 5-hour drive and Providence, which is a 3-hour drive. If you are planning to drive to Portland and don’t want to use the miles on your car, it is recommended that you rent one. In addition, if you aren’t from the Northeast of the United Sates or Canada, you could fly into Portland International Jetport or Portsmouth International Airport at Pease. You could find affordable flights through Skyscanner.

Looking for an RV for your next trip, reserve here!

Where to Stay in Portland, Maine during a Long Weekend:

Sunflower in Portland, Maine

When it comes to finding accommodation in Portland, Maine there are a variety of hotels and rental properties to choose from, based on budget, for your long weekend getaway.

My friend and I stayed at Portland Sheraton at Sable Oaks in South Portland. It was about a 10 minute drive to the heart of the city. (There are Ubers and Lyfts in Portland as well. When we went out, we took advantage of either one of these services.)

In addition to hotels, you could also choose from a selection of Airbnb and Vrbo options within the Portland area. Click here to check out the hotels in and around Portland. Below are my recommendations:

Luxury Accommodation: The Press Hotel, Autograph Collection

Boutique Accommodation: Portland Harbor Hotel

Mid-Budget Accommodation: The Francis

Budget Accommodation: Holiday Inn Portland

Long Weekend Itinerary for Portland, Maine:

Spring Point Ledge Light in Portland, Maine

Day 1 in Portland, Maine:

Savor Dinner on the Wharf:
A crab roll from Boone's Fish House in Portland, Maine

When my friend and I arrived in Portland, Maine for our long weekend, we couldn’t wait to start exploring! I was also excited for some fresh seafood.

Since we arrived a little later in the day, we settled into our hotel and then headed to a warm and welcoming waterfront restaurant on Portland’s famous Commercial Street called Boone’s Fish House & Oyster Room. When we arrived in Portland, it was cold and rainy, so Boone’s was a great place to warm up since they have several fireplaces and a great selection of Portland-brewed beers.

For dinner, I ate a delicious crab roll on a brioche bun and my friend had the lobster mac and cheese. All of Boone’s seafood is fresh and delivered right to the restaurant from the water.

Grab After Dinner Drinks:
Commercial Street in Portland, Maine

Our first night took us through history as we made our way around the cobblestoned streets. (Portland is such a lovely city to stroll around during a beautiful evening!) The first stop of the night was at Vena’s Fizz House, a corner-side cocktail house with a charming turn-of-the-century atmosphere.

Vena’s offers a plethora of drink options for all ages that features fresh ingredient fizz drinks that are both alcoholic and non-alcoholic along with mocktails and cocktails. The adorable bar even has a boutique that offers Vena’s mixology of syrups, infusions and other ingredients to create your own craft cocktails at home.

The best part about Vena’s is that their drinks aren’t too strong. I know everyone has his or her own drink preferences, but I cannot enjoy something when all I taste is alcohol. I ordered a Maple Syrup Switchel that consisted of rum, fresh Maine maple, molasses, ginger, coffee and aromatic bitters. I was able to savor every flavor and it was unforgettable.

After enjoying some time at Vena’s and getting to know the friendly owners, we took the party over to a local Portland bar on Commercial Street called Three Dollar Dewey’s. This dive bar is a great place to get cheap beer and meet friendly people.

Day 2 in Portland, Maine:

Enjoy Coffee and Brunch in Old Port:
Two women enjoying a long weekend getaway in Portland, Maine

Our second day during our long weekend in Portland, Maine was absolutely gorgeous! We wanted to take advantage of the sunny weather, so we headed back into Old Port (downtown Portland) to walk around and grab a freshly brewed cup of coffee at Coffee by Design on Congress Street (there are a few locations throughout the city).

After walking around the neighborhoods with our coffee and admiring all of the cute New England architecture, we were starving for a delicious breakfast.

Brunch at Little Tap House during a long weekend in Portland, Maine

Portland is known to have many great brunch spots, so we had many options to choose from. Since we were in the area, we stopped at an adorable farm-to-table gastro-pub called Little Tap House.

When we walked inside, all of the furniture pieces were rustic and the decorations were colorful and charming. I savored a delicious breakfast bowl of home fries, caramelized onion, locally sourced mushrooms, peppers and scallions topped with fried eggs with a mimosa on the side. It definitely hit the spot!

Stroll around Portland’s Promenade:
Coastal towns near Portland, Maine

Once we finished brunch, we were full, so a walk around the city was well needed. We walked down Congress Street, through a few neighborhoods, before we hit the Eastern Promenade – a breathtaking costal trail, built along an old rail corridor that offers beautiful views of the harbor and Casco Bay.

Since it was a gorgeous day, there were plenty of sailboats in the water, people were hanging out on the lawn and East End Beach and, of course, their adorable puppies were playing in the chilling water. This 2.1-mile trail allows people to bike, run, bird feed, dog walk and enjoy the day. You can even take a train ride around the promenade and learn more about this wonderful seaport city.

Overall, enjoying the Eastern Promenade is a must-do during a long weekend in Portland, Maine.

Admire the Picturesque Lighthouses:
A woman at Spring Point Ledge Light during a long weekend trip to Portland, Maine

The afternoon took us over to South Portland to see the lighthouses. Even though I have spent every summer at the Jersey Shore, I had never seen a lighthouse in real life prior to this trip. (There is one in New Jersey on Long Beach Island.) Over the years, I have seen lighthouses in Malta, Portugal, Cape May and Delaware.

The first lighthouse we saw during our long weekend in Portland, Maine was the Spring Point Ledge Light, right off the Southern Maine Community College campus. The Spring Point Ledge Light is a dangerous obstruction on the west side on the main shipping channel.

Unlike many of the lighthouses, this tower is built of brick instead of cast-iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse.

Unfortunately, on the day we went, we were unable to tour the inside of the lighthouse, but it was still cool to walk up to it and enjoy the views of the harbor, pebble beaches, historic forts and the beautiful Casco Bay. I definitely recommend wearing comfortable shoes when you walk across the breakwater because there are a lot of ways you can fall and get hurt.

Fort Williams Park in Cape Elizabeth

After our time at Spring Point Ledge Light, we drove 15 minutes into the affluent town of Cape Elizabeth to the stunning Fort Williams Park. The beautiful park features 90 acres of rugged beauty along the Casco Bay.

There are also several hiking paths with beautiful cliffside views of the water crashing onto the rocks. In addition, there are many great lookout spots, a rock beach, picnic areas, a playground, ball fields and more!

Seeing Portland Head Light during a long weekend in Portland, Maine

As you continue to walk south, you can catch a stunning view of the symbolic Portland Head Light, modeling its beauty on the coastal cliffs of Cape Elizabeth.

The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the beautiful lighthouse reminded us of why we chose to come to Maine in the first place.

Overall, Portland Head Light and Fort Williams park are absolutely breathtaking and you cannot visit Portland, Maine during a long weekend trip and not come to this spot.

Eat the Best Lobster Rolls:
Bite Into Maine in Fort Williams Park

Before visiting Maine, I read on a few travel blogs that the best lobster rolls were found in a small airstream in Fort Williams Park called Bite Into Maine.

Since the airstream is so small, we had a tough time trying to locate it, but it gave us the opportunity to explore the park more and interact with the locals. We finally found it and indulged in mouthwatering fresh Maine lobster chunks on a warm bun. There are so many types of lobster rolls for you to choose from through Bite Into Maine.

Have a Chowder Dinner in Portland:

I was recommended by a friend to check out Gilbert’s Chowder House right off the wharf on Commercial Street. During our second evening in Portland, I was in the mood for a warm soup, so I was thrilled to give this place a try!

New England Clam Chowder

I savored a delicious New England clam chowder in a freshly baked bread bowl. It was the perfect light dinner and Gilbert’s offers a warm and welcoming atmosphere.

Have a Fun Night Out in Portland:

The night took us over to Bull Feeney’s, which is a fancy Irish tavern located on Fore Street that offers something for everyone to enjoy. (New England has a heavy Irish influence.)

On the bottom floor, you can grab a drink and sit down at one of their tables and talk with friends. The second story has a dance floor with a room off to the side that hosts Maine’s best cover bands. You can even get seated service and enjoy a lovely Irish brunch or dinner.

Day 3 in Portland, Maine:

A woman enjoying a long weekend in Portland, Maine discovering coastal towns
Adventure through Southern Maine’s Beaches:
A woman at Old Orchard Beach in Southern Maine

Originally, my friend and I were supposed to do a day trip to Acadia National Park in Bar Harbor, but it was further away than we thought for a day trip. (Looks like I have to make my way back up to Maine.) However, we did end up exploring the beautiful beaches south of Portland to make up for it!

Below are beach towns to include in a long weekend itinerary for Portland, Maine.

Visiting Biddeford Pool, Maine during a long weekend getaway to Portland, Maine

Old Orchard Beach: A half hour south of Portland is Old Orchard Beach. We started our fun day there where we grabbed breakfast, wandered around the boardwalk as well as walked on the beach. (We enjoyed breakfast at Joseph’s by the Sea.)

A seaside walking trail in Biddeford Pool, Maine

Biddeford Pool: This secluded coastal town has beautiful cedar houses and a breathtaking rock beach. Even though it was Memorial Day Weekend when we traveled to Biddeford Pool, there wasn’t a soul around!

We walked around the rock beach towards the white sand beach. The cool part about these beaches is that they have a small hiking trail through the woods and meadows that you walk through to get to them. During our time there, we got to see a lot of stunning birds.

The beach at Kennebunkport

Kennebunkport: The small town of Kennebunkport is just as beautiful as Biddeford Pool, except there were more people. I loved all of the colorful trees in the beach area. It was so breathtaking! We also enjoyed walking around the downtown area and grabbing some coffee, snacks and more before heading back to Portland.

Enjoy a Fancy Dinner in Portland:

During our last evening in Portland, Maine, we wanted to get a nice dinner on the water. Since the weather was beautiful, we were able to enjoy a beautiful sunset and savor delicious lobster rolls (for one last time) at DiMillo’s on the Water. Instead of getting drinks afterwards, we ended up grabbing dessert at Gorgeous Gelato.

Day 4 in Portland:

A woman on the beach at Biddeford Pool near Portland, Maine during a long weekend
Savor Donuts for Breakfast:

It was raining pretty hard during our last morning in Portland, so we wanted to get on the road early. We first stopped at The Holy Donut located in Old Port before hitting the road. Their donuts are delicious and made with locally grown potatoes. It was tasty, unique and the perfect way to end our time in Portland.

Click here to discover more to do in Portland, Maine during a long weekend.


A woman at Biddeford Pool during a long weekend in Portland, Maine

I hope you all enjoyed reading about my long weekend getaway itinerary for Portland, Maine. If you have any questions about my time in Portland, please email me at [email protected]

Make sure to pin this post if you find it useful!

A long weekend itinerary for Portland, Maine

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., ME State Capital: Augusta, Time Zone: Eastern Standard Time

Click here to join my private blog sharing Facebook group.

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Portland, Maine Look:

22 Comments

  1. Merrie Rodriguez on August 15, 2019 at 11:43 pm

    This is my husbands DREAM vacation!! We are hoping to get there ASAP lol!

    • Taylor Deer on August 16, 2019 at 9:17 am

      Portland is so beautiful, you guys would love it so much! If you have the time too, I recommend visiting Acadia National Park too.:)

  2. Anna on August 16, 2019 at 11:59 am

    It sounds like a wonderful way how to spend a long weekend ♥!
    And Donuts for breakfast – seriously?? That must be soo amazing :D!!!

    • Taylor Deer on August 16, 2019 at 12:38 pm

      Yes, it was quite lovely and Maine is so peaceful! lol yes, I need to do better about not having donuts for breakfast, but they are amazing! 🙂

  3. Aswani on August 16, 2019 at 2:25 pm

    Didn’t realize there is a Portland in Maine! Gorgeous picture Taylor. Makes me want to visit this place!

    • Taylor Deer on August 17, 2019 at 5:18 pm

      Yes, it’s so beautiful and the seafood is amazing! You definitely have to go at some point.

  4. Amanda on July 28, 2020 at 10:56 am

    I’m wondering where you saw that pretty white building? Which beach and how did you get there? Thank you!

    • Taylor Deer on July 28, 2020 at 11:03 am

      Hi Amanada, If you’re referring to the white hotel on the beach, that was in Biddeford Pool, Maine. Overall, Biddeford isn’t a big town and it’s very quiet. You could easily walk around the beach and find it, that is what we did. We mainly walked around the East Point Sanctuary. Honestly, I don’t know the name of the hotel and I even tried looking it up and couldn’t find it. I visited in 2017, so it possibly may not even be there anymore. I couldn’t tell if it was abandoned when I was there.

  5. Cosette on June 3, 2021 at 6:25 am

    Such a beautiful area of the USA. I haven’t been to this part yet, but it looks so beautiful. The food also looks delicious.

    • Taylor Deer on June 3, 2021 at 9:30 am

      New England truly is beautiful and I love all of the seafood there. 🙂

  6. Puloma Banerjee on June 12, 2021 at 12:24 pm

    Wow such an amazing post on Portland, Maine. The scenic beaches and landscape is tempting and so is the seafood! Makes me want to visit it!

    • Taylor Deer on June 12, 2021 at 8:33 pm

      Thank you so much Puloma! It really is such a beautiful part of the country. 🙂

  7. Monica on June 12, 2021 at 10:31 pm

    Maine is just so beautiful in the photos. I would love to know more about campgrounds in the state.

    • Taylor Deer on June 13, 2021 at 11:08 am

      It really is such a beautiful state. I don’t know much about camping there, but I can imagine it is wonderful! 🙂

  8. Brianna on June 12, 2021 at 10:41 pm

    I loved Portland and especially Vena’s Fizz House! Looks like you had perfect weather too.

    • Taylor Deer on June 13, 2021 at 11:09 am

      Yes, it is such a cute spot! I’d love to go back. I went during Memorial Day Weekend in 2017 and it was quite chilly, but we were lucky with no rain. 🙂

  9. Vanessa on June 13, 2021 at 8:15 am

    Looks like you did all the quintessential things when visiting Maine! I pinned this post as I’ve always wanted to visit the state. Oh, those lobster rolls and a bowl of clam chowder are calling my name.

    • Taylor Deer on June 13, 2021 at 11:10 am

      The seafood there is some of the best in the world! You would love Portland Vanessa. 🙂

  10. Linda (LD Holland) on June 13, 2021 at 3:24 pm

    We spent a week on the coast but only got a few hours in Portland. But we did find some great seafood for lunch one day! I can see that next time we need to spend some more time there. A great base to see the lighthouses along the bay.

    • Taylor Deer on June 14, 2021 at 4:46 pm

      Yes, it is such a nice city! I loved all the seafood there. 🙂

  11. Emilia Taneva on June 13, 2021 at 5:32 pm

    I love Portland! One of my best friends live there but I haven’t been in years. Your trip and photos look so fun!

    • Taylor Deer on June 14, 2021 at 4:49 pm

      It is such a great city! 🙂 Thank you!

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