Western Catskills in New York: The Best Fall Getaway

There’s nothing like visiting the Northeast of the United States during autumn, especially in New York State. You can admire the vibrant fall foliage, enjoy perfect hiking weather, stay at charming and cozy accommodations and savor delicious local food. One of the best places to travel to enjoy a fall getaway is the Western Catskills!

During the fall of 2022, I did an autumn weekend getaway to Sullivan County in Western Catskills with Caitlin of My Darling Passport and Chantilly of Chantilly Songs. Overall, Sullivan County in West Catskills makes for one of the best fall getaways from NYC. It boasts numerous hiking trails, glamping sites, breweries and cideries, small towns, great eateries and wonderful memories to be made!

If you’re wondering, the difference between the Eastern Catskill Mountains and the Western Catskill Mountains is that the eastern mountains are higher in elevation. In contrast, the western mountains flatten into the Allegheny Plateau. Discover the best things to do during fall in the Western Catskills in this article!

**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. My fall trip to the Western Catskills was in partnership with Sullivan County Visitors Association.

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Traveling to the Catskill Mountains:

Sullivan County in Western Catskills is easy to get to, especially from the Tri-State area and Pennsylvania. Depending on where you’re traveling from in neighboring states, it can take an hour to four hours to get to Sullivan County via a road trip. The major highways to take that will get you to Sullivan County are I-87, Route 17, I-84, I-90 or I-88.

If you fly to the Western Catskills, the closest international airports are New York Steward International Airport in Newburgh/New Windsor, NY and Sullivan County International Airport in Swan Lake, NY. You can find affordable flights through Skyscanner. Unless you have a vehicle, you must rent a car to get around Sullivan County.

Another way to get to Sullivan County for a fall getaway to the Catskills is by taking the ShortLine Bus into Monticello Bus Terminal. You can quickly get it from the Port Authority Bus Terminal in Manhattan.

Please note that most popular ride-sharing services are unavailable in Sullivan County since it’s more rural. Still, there are the Yellow Cab taxi services that are based out of Monticello. Also based in Monticello is Move Sullivan, a transportation service available to all Sullivan County residents and visitors.

Click here if you are planning to road trip around the United States and want to rent an RV.

Where to Stay in the Western Catskills:

Antrim Streamside in Livingston Manor, NY, is the best place to stay in Sullivan County in the New York Catskills. They are luxury boutique cabins and cottages in a gated estate on the Willowemoc River in Upstate New York.

Overall, Antrim Streamside is the perfect place to stay during a fall getaway to the Western Catskills. Each cabin and cottage have a private entrance and features a kitchen, organic cotton mattresses that are comfy, modern and spacious bathrooms, custom amenities, heat/air conditioning, WiFi and beautiful views.

What is great about staying at Antrim Streamside is that you don’t have to leave the property to have an enjoyable fall adventure! There are glistening ponds, an apple orchard, and 250 acres of woodlands filled with fascinating wildlife, along with walking and hiking trails.

Antrim Streamside also has hammocks, swings, Adirondack chairs, picnic tables and fire pits to relax with a book, bottle of wine and great company during the fall season. During a stay at this wonderful Upstate NY fall resort, you can also book a massage service, yoga session, a private fishing guide and a gourmet dinner made by a personal chef. I loved how Antrim Streamside had all the amenities you’d get at a luxury hotel!

Also located at Antrim Streamside is a dreamy suspension bridge that lights up at night. It’s perfect for romantic strolls, photo opportunities and leaf-peeping! Antrim Streamside is also great for special celebrations like weddings.

The Best Fall Getaway – Adventure to Western Catskills

There’s nothing like Fall in the Catskills! From experiencing the top hiking trails to enjoying the best fall foliage, the heart of the Western Catskills will leave you awestruck. Plus, there are plenty of great things to do during a Catskills girl’s weekend getaway!

During October, the weather in Western Catskills range from highs in the low 60s°F to lows in the upper 30s°F with an average of eight rainy days. It’s essential to bring warm clothing for your Catskills getaway!

Get Spooked at Peace, Love & Pumpkins at Bethel Woods:

A fall getaway to the Catskills is incomplete without experiencing Peace, Love & Pumpkins at Bethel Woods Center for the Arts in Bethel, New York. Enjoy this fun Halloween event from 6:30 pm to 10 pm from mid to late October. It also costs $23 USD for adults 18 years and older, $13 USD for kids and teens ages 3-17 and free for children under 2 years old.

Bethel Woods is where the 1969 Woodstock festival took place. Nowadays, it’s a concert hall, museum and exhibit gallery that hosts great shows and events like Peace, Love & Pumpkins.

During October, get into the spooky season spirit by enjoying the garden trails where you can admire hand-carved Jack O Lanterns, glowing pumpkin art and fun Halloween displays. On Friday, Peace, Love & Pumpkins offer a spookier experience for adults only from 6:30 pm to 11 pm. This event is one of the top reasons why visiting Sullivan County is a great fall getaway to the Catskills.

Have a Fun Fall Day at Upward Brewing Company:

One of the best places to visit in Western Catskills is Upward Brewing Company in Livingston Manor. It’s a fun brewery with great craft beers, delicious bites, an outdoor fire pit, an indoor beer garden, a serene pond, cozy fireplace and scenic walking trails.

At Upward Brewing Company, you can choose from a selection of lagers, ales, IPAs, stouts and more. The cozy fall vibes at this spot are also on point and Upward Brewing Company will also host local bands that will play live music during the day and in the evening.

Not only is Upward Brewing Company known for its beer, but there is also great food to savor! We shared Bavarian pretzels, bratwurst, fish tacos, Buffalo cauliflower bites, mozzarella sticks and Southern chicken dumplings.

When you spend a fall day at Upward Brewing Company with girlfriends, you will have the best time! It makes Sullivan County one of the best NYC fall getaways for friend groups.

Savor Delicious Pizza at The Kaatskeller:

A local favorite you must visit for lunch or dinner during your fall getaway to the Catskills is The Kaatskeller in Livingston Manor. You can enjoy this spot’s best wood-fired pizzas, salads and cocktails.

What also makes The Kaatskeller one of the best places to visit in the fall is its cozy indoor seating on a cooler evening, a lively outdoor garden with stringed lights, fire pits, live music and more. Also located at this thriving spot is The Milkweed Gelato Camper for dessert during the warmer months!

During our time at The Kaatskeller, I had the Saltwater pie, a New Haven-style white pizza with littleneck clams, arugula and lemon; Chantilly had the White Album pie, which had house-made wild ramp kale pesto, bacon jam, goat cheese, aged Parmigiano-Reggiano, egg, broccoli shoot and extra virgin olive oil and Caitlin had The High Life pie, which is a Margherita pizza with local mozzarella, San Marzano tomato sauce, Agrarian Feast micro basil and extra virgin olive oil.

Walk through the Farmers’ Market in Callicoon:

Located in downtown Callicoon, along the Delaware River, is a farmers’ market every Sunday from 11 am to 2 pm.

At the Callicoon Farmers’ Market, local vendors and food producers sell fresh produce, artisan wines, hard cider, homemade jams, maple syrup and products, baked goods and more. During the fall season, you can also purchase different pumpkins, autumn décor, seasonal products and clothing for cooler weather.

Sip Apple Ciders and Admire Scenic Views at Seminary Hill Orchard & Cidery:

Another great place to visit during a fall getaway to the Western Catskills is Seminary Hill Orchard & Cidery in Callicoon. It’s one of the most beautiful cideries I’ve been to in North America and also one of the best places in the Catskill Mountains.

Seminary Hill Orchard & Cidery boasts an orchard-to-bottle experience using their own apples and pears for their cider. This location is home to a Catskills hotel, seasonal restaurant and event space. It also lets you experience the agricultural heritage of historic Callicoon and the Delaware Valley.  

Spending an afternoon at Seminary Hill Orchard & Cidery is the best way to enjoy a Western Catskills weekend getaway. There’s a tasting room, dining room, outdoor patio and lawn area to appreciate the Catskills fall foliage. There are also fire pits at this lovely spot where you can relish breathtaking views of the Delaware River and the nearby Pocono Mountains.

The three of us enjoyed cider flights. We also savored an incredible charcuterie board and roasted butternut squash as appetizers, along with farm-to-table delights with local ingredients such as trout with roasted potatoes and cider beurre blanc as well as roasted duck with chestnuts and matsutake mushrooms as our main meals.

Enjoy the Best Fall Foliage on a Fun Hike in New York’s Catskills:

Another reason Sullivan County is one of the best long weekend getaways in the Catskill is the variety of outdoor activities in the fresh mountain air! Below are the best hikes and ways to enjoy the great outdoors in the Western Catskills:

Adler Lake to Balsam Lake Mountain Fire Tower: One of the best hikes in Sullivan County is this 13-mile, out-and-back trail near Margaretville. It’s a difficult hike with a 2,841-foot elevation gain.

During this hike, you’ll start in Balsam Lake Mountain Wild Forest to Alder Lake and continue along the Mill Brook Ridge Trail. At the summit, there is a fire tower and breathtaking views.

Red Hill Fire Tower Trail: This is a fun moderate hike in Sullivan County near Claryville. It’s a 3.7-mile, out-and-back hike with a 1,076-foot elevation gain. Please note that although this hike is beautiful, it’s highly trafficked since it’s one of the most popular.

Diamond Notch Falls: One of the best hikes to do in Western Catskills that I did with a friend a year prior is Diamond Notch Falls via Diamond Notch Road. It’s a 4-mile, out-and-back trail near Lanesville in Greene County.

Overall, this hike is challenging, but it’s beautiful! The best time to do it is when the leaves boast bright colors in the fall!

Neversink River via Hiram Jones Road: The Neversink River is iconic to Sullivan County and there are a lot of excellent hikes to enjoy around it. This hike around the Neversink River Unique Area includes an easy, 3.6-mile, out-and-back trail near Rock Hill.

This trail is also great for camping, fishing and exploring during the fall months. It’s one of the top reasons why the Western Catskills is one of the best fall getaways in Upstate New York, for all ages, during autumn.

Frost Valley YMCA: Also located in Sullivan County is Frost Valley in Claryville. It’s a camping and environmental education center along the Neversink River that is great for family outings and kids’ adventures. (I went to Frost Valley YMCA during a weekend school trip when I was 11; it was my first outdoor experience.)

At Frost Valley, you can enjoy one of the many hiking trails, as well as go rock climbing, boating, zip lining, stargazing and fishing. You can also participate in different sports, yoga, archery, horseback riding, kayaking, bird watching and more. You’ll make loads of family fun memories at Frost Valley!

(If you’re looking for an intimate yoga retreat in Western Catskills, Heathen Hill Yoga offers a heavenly escape to rest and recharge. It’s located in Franklin in Delaware County. During your retreat, you can enjoy different yoga workshops, delicious vegan meals, candle-making classes and meditations. You can also go swimming in the pond and make new friends.)

Wander through the Charming Towns of Livingston Manor and Callicoon:

Livingston Manor is Catskill’s newest hot spot behind Phoenicia and Woodstock! On Main Street, you can find different restaurants, bars, clothing boutiques, art galleries and other small businesses.

The restaurants on Main Street in Livingston Manor are Upward Brewing, The Kaatskeller, along with The DeBruce for fine dining, Smoke Joint for barbecue and Main Street Farm for farm-to-table.

You must shop at Long Weekend for vintage furniture and lighting; Homestedt for outdoor essentials; Upstream Wine & Spirits for natural wines and international favorites, like orange wines and Nest for chic fashion and Scandinavian home goods.

The charming downtown area of Callicoon is another reason you should do a fall getaway to the Catskills this year! Located next to the Delaware River, there’s a lot this town has to offer and it’s where you’ll find many city dwellers. It’s also one of the most walkable towns in the Catskills!

In addition to Seminary Hill Orchard & Cidery and the Sunday Farmer’s Market, you must also check out the Western Hotel, which is a National Historic Landmark; Callicoon Brewery Company for fresh local beer; Catskill Provisions Distillery for a cocktail; Peppino’s Family for the best pizza in Callicoon; The Callicoon Theater, which is a retro-style venue where you can see a show; Callicoon Wine Merchant for a glass of wine and Spruce Home Goods for vintage home décor and scrumptious apple cider donuts!

See Russell Brook Falls in Roscoe:

One of the most scenic spots in Sullivan County is Russell Brook Falls in Roscoe. From Morton Hill Road, there is a short walk to the falls. Just cross a small footbridge and a stream will lead you to the waterfalls.

It’s a beautiful spot to visit if you’re not looking to do a long or strenuous hike. There is a small swimming area to enjoy on a warm day, but the colorful foliage will leave you in awe during autumn.

Go Pumpkin Picking at Cunningham Family Farms:

The New York Catskills is the perfect place to do all the best fall activities in October! Cunningham Family Farms in Swan Lake offers pumpkin picking, a corn maze, hayrides and autumn-baked goods to enjoy like fresh apple and pumpkin pies and cider donuts!

Cunningham Family Farms boasts the most giant corn maze in Sullivan County and presents a challenge for all age groups. Regarding hayrides, you can ride to the patch and get spooked on a ghosts and ghouls tour during the Halloween season.

Do a Day Trip to the Hudson Valley:

There are plenty of great day trips from Sullivan County, two of which are to enjoy the Hudson Valley and Eastern Catskills. Below is a list of the best things to do during a day trip from the Western Catskills in the fall:

• Hike around and enjoy Mohonk Mountain House in New Paltz.
• Enjoy crisp ciders at Angry Orchard Cider House in Walden.
• See Kaaterskill Falls in Hunter.
• Stroll around the town of Phoenicia.
• Attend Oktoberfest at Hunter Mountain, Bear Mountain or Kruckers in Pomona.

Discover other similar trips to take during the fall:

• The Perfect Getaway House in the New York Catskills
• Fall in the Berkshires
• Visiting Salem, MA during Halloween

I hope you all enjoyed discovering the best things to do during a fall getaway to the Catskills. If you have any questions, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

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

*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.

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