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Guide to a Fall or Winter Getaway in the Great Northern Catskills

Updated: Mar 30, 2023

The weather is turning which means it’s time to explore all the Great Northern Catskills has to offer in the fall and winter! From spending time outdoors, to eating and drinking your way through the top restaurants in the area, there is something for everyone. Here are our top suggestions for how to spend your time on your next seasonal trip to the Catskills.

Catch a Gig at Avalon Lounge

Avalon Lounge has all the trendy, chic (and cozy!) vibes you could ask for. From indie rock to jazz, they offer shows every Wednesday - Sunday. Come hungry because they offer homestyle Korean food from Annie’s Kitchen that you don’t want to skimp on.

Shop on Main Street in Catskills, NY

Grab a coffee and enjoy the artwork from rotating artists at HiLo before making your way down Main Street. From delicious bites, to boutiques, to books, records, and game stores — Main Street in the Catskills has a shop for everyone.

Take a ride through the Catskills, the old fashioned way

Whether it’s by trolley, train, or rail explorer, the Catskills give plenty of opportunities to catch a uniquely designed scenic ride. If you’re looking for a calm eye-catching ride throughout the month of October, hop on the Kaaterskill Trolley. The ride lasts 2.5 hours with stops at Kaaterskill Falls as well as the Mountain Top Arboretum to take in the view and get some photos! The Catskills Rail Explorer brings in an interactive experience fit for all ages. They offer weekend and weekday river run tours along with evening lantern tours, each tour lasting around 2.5 hours! The Catskill Mountain Railroad transports you back in time through its old-time train ride experience. Although it runs from March-December, we recommend planning an outing for one of their specialty rides. In September and October, they run their Fall Foliage and Pumpkin Express Rides and in November and December, hop on board the Polar Express!

Eat and Drink your way through the best Restaurants and Breweries in the Area

Greene County has a wide array of culinary experiences waiting to be enjoyed during your fall or winter getaway. Check out our top “bites and brews” in the area here.

Visit a Historic Site

Walk between two prominent historic sites via the Hudson River Skywalk at the Rip Van Winkle Bridge. This 3 mile walkway overlooks views of the Hudson Valley as well as the Catskill Mountains and connects the famous Fredrick Church's Olana and the Thomas Cole National Historic Site, both famous Hudson River School artists.

Plan a route through one of Catskills Scenic Byways

Mountain Clove Scenic Byway is a 41 mile stretch through the Northernmost Peaks of the Catskill Mountains offering experiences for the body, mind, and soul! Plan an excursion with scenic views, historical and cultural learning, as well as recreational experiences. Durham Valley Scenic Byway is a 21 mile stretch through Durham and Windham. Also providing rich scenic and historical perspectives that shouldn’t be missed!

Head to the 5 State Lookout

Also part of the Durham Valley Scenic Byway is the 5 State Lookout. We recommend taking a pit stop off Route 23, for gorgeous views that span 5 different states. On a clear day, this lookout spot captures views of the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York, and the Connecticut Valley. Unfortunately there isn’t a sign describing the view, so make sure to bring your compass.

Explore all that Hunter and Windham Mountain have to offer

Enjoy Hunter Mountain’s Colors in the Catskills Fall Festival in October and skiing for all levels throughout the winter. With a new chairlift and nine new trails, this ski resort offers a vast variety of terrain across 3 mountains ranging from easy green to double black diamond slopes. Not far from Hunter Mountain, you’ll find Windham Mountain, which also offers a wide array of skiing options as well as a tubing park and the Alpine Spa for those that need a break from skiing! Both resorts have a wide array of dining options as well!

For those looking to plan a trip with family or friends to the Great Northern Catskills, check out @bugghaus on instagram, Airbnb, and VRBO for a unique and cozy accommodation option!

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