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Things To Do

The Catskills are a beautiful place to spend a fall weekend, with scenic drives, great restaurants, hiking trails, and charming small towns throughout the region. Early October is the best time of year to visit, with peak fall foliage in the mountains. If you have time while you’re in town, we recommend exploring nearby towns, stopping by a local café or brewery, or getting outside for a walk or hike. Below are a few of our favorite spots in the area.
Kaaterskill Falls

Kaaterskill Falls

Kaaterskill Falls, Hunter, NY 12436

One of the most iconic natural landmarks in the Catskills, Kaaterskill Falls is a stunning two-tiered waterfall surrounded by mountain scenery. There are a few ways to experience it, from a scenic overlook to a short hike nearby, making it an easy and worthwhile stop if you have time to explore.

Deer Mountain Inn

Deer Mountain Inn

790 County Road 25, Tannersville, NY 12485

A beautifully restored 19th-century inn known for its seasonal restaurant, cozy bar, and mountain views. This is one of our favorite places in the Catskills. The inn will be closed for a wedding during our weekend, but if you’re arriving a few days early or staying a bit longer, it’s a wonderful spot for dinner or drinks.

Fellow Mountain Cafe

Fellow Mountain Cafe

7883 Main Street, Hunter, NY 12442

A cozy café in Hunter known for great coffee, thoughtful breakfast and lunch, and a relaxed mountain-town atmosphere. A perfect stop to start the day if you’re exploring the area.

West Kill Brewing

West Kill Brewing

2173 Spruceton Road, West Kill, NY 12492

Tucked into the mountains, West Kill Brewing is Eric’s favorite spot and one we always make time for when we’re in the Catskills. Set on a former family dairy farm, the brewery is known for its small batch beers made with local ingredients and mountain spring water. It’s the perfect place to spend a relaxed afternoon with great beer and mountain views.

The Windham Local Public House

The Windham Local Public House

5410 New York 23, Windham, NY 12496

A cozy spot right in the heart of Windham, it's perfect for a casual meal or coffee stop. The menu is big with something for everyone, and the food is consistently good, whether you’re stopping in for brunch, coffee, or a relaxed dinner.

Hotel Lilien

Hotel Lilien

6629 New York 23A, Tannersville, NY 12485

A beautifully restored boutique hotel tucked into the mountains of Tannersville, Hotel Lilien is a great spot in the area for a cozy drink or relaxed evening. Their bar and lounge will be open Thursday and Sunday and is absolutely worth stopping by for cocktails and light bites. *The hotel is fully booked Friday and Saturday for a private wedding buyout.

The Henson

The Henson

39 Goshen Road, Hensonville, NY 12439

The Henson is a boutique hotel in the Catskills that’s home to Matilda, an upscale restaurant and bar known for dinner, dessert, and cocktails. The backyard gardens are beautiful too. The property will be open to the public Wednesday through Sunday, though it will be closed Saturday for a private wedding buyout. All accommodations are reserved for the wedding onsite. *make a reservation here asap if you plan on getting into town early or staying a bit longer.

Paracasa

Paracasa

391 New York 296, Hensonville, NY 12439

Located in Hensonville. Grab-and-go provisions, coffee, matcha, and some great baked goods.

Hunter Mountain Scenic Skyride

Hunter Mountain Scenic Skyride

A scenic chairlift ride to the summit of Hunter Mountain (4,040 ft) with sweeping views of the Catskills. At the top you’ll find walking trails and lookout points, making it an easy way to take in the mountains without a long hike.

Phoenicia Diner

Phoenicia Diner

5681 New York 28, Phoenicia, NY 12464

A Catskills classic, Phoenicia Diner dates back to the early 1960s and has become a staple in the area. It’s a go to spot for a laid back breakfast or lunch, with locally sourced ingredients and elevated diner favorites. Perfect before or after a day of exploring.

The Windham Path

The Windham Path

4982 New York 23, Windham, NY 12496

A scenic, easy walking trail with mountain views, meadows, streams, and a covered bridge. Perfect for a morning stroll, run, or bike ride. Guests staying at Wylder can easily access the path right from the hotel area.

Fred's Coffee & Donuts

Fred's Coffee & Donuts

6715 New York 23A, Tannersville, NY 12485

Fresh donuts, breakfast sandwiches, and coffee, plus a convenient drive-thru. Great for a quick breakfast on the go.

Overlook Mountain Trail

Overlook Mountain Trail

Overlook Mountain Trail, NY

A popular hike just outside Woodstock that leads to sweeping views of the Hudson Valley. The trail follows an old carriage road to the summit, passing the ruins of the historic Overlook Mountain House along the way.

Woodstock

Woodstock

Woodstock, NY

A charming town known for its creative, laid-back vibe, with great shops, galleries, cafés, and restaurants throughout the center of town. While the famous 1969 Woodstock festival was actually held about an hour west in Bethel, the town still carries the artistic spirit it became known for in the 1960s. It’s a great place to wander for an afternoon — we recommend grabbing coffee, browsing the local shops, and exploring the small galleries around town. We love SILVIA, Good Night, Bread Alone Bakery and Mud Club.