The best things to do in Windham, NY in the fall involve immersing yourself in the great outdoors of the Catskill Mountains!
Located in Greene County about 2.5 hours north of New York City, Windham is a well-known winter destination, attracting downhill skiers looking to hit the slopes at Windham Mountain. But the endless opportunities for outdoor recreation like hiking and mountain biking make the mountain resort town an all-season destination.
Hiking in Windham, NY is plentiful, with access to many scenic hiking trails ranging from easy to difficult. The numerous hiking trails make autumn, especially, a magnificent season to visit. Hikers can take leisurely nature walks on easy trails, or hike on more rugged terrain to several Catskill high peaks.
Expertly groomed mountain biking trails, especially those at Windham Mountain Bike Park, also attract outdoor enthusiasts.
A historic main street ties the hamlet together, with plenty of cafes, restaurants, and boutiques to explore.
If you love the changing colors of fall, there’s no better place to experience them than Windham, whose nickname alternates between “Land in the Sky” and “Gem of the Catskills.” Read on for the 13 best things to do in Windham, NY in the fall. You’ll also find recommendations for area hotels and restaurants.
1. Hike to Acra Point
With its location in the heart of the Catskills, there are some amazing opportunities for hiking in Windham, NY, and believe me when I tell you that autumn in the Catskills is magnificent!
When we plan our hikes, Matt and I usually look for moderate trails with a rewarding view at the top. That’s exactly what we found when we hiked to Acra Point.
Parking
Park at Big Hollow Parking Area at the end of Big Hollow Road in Maplecrest. When we arrived at around 10:30 a.m. on a Saturday, the actual lot was full but there was plenty of parking on both sides of the road.
Hiking
From Big Hollow Parking Area, follow the red trail blazes. The trail is clearly marked and well-maintained in a beautiful forest setting. Batavia Kill creek crosses the trail several times, forming small waterfalls along the way.
Hikers follow a steady incline almost the entire way up to Acra Point, though there are some points where the trail levels out briefly. You’ll have to cross narrow sections of the creek a couple of times. Large rocks are in place to assist you but use caution as the rocks may shift when you step on them.
The trail also has a couple of rock ledges, which requires the use of arm and leg strength to hoist oneself up a few feet.
One mile into the red trail, you’ll encounter the blue trail junction. From here, follow the blue blazes to Acra Point (.7 miles). You can also follow the blue blazes to the left, which lead to Burnt Knob (1.5 miles) and Windham High Peak (2 miles).
According to the trail map, the blue trail markers indicate the Catskills Escarpment Trail. Acra Point, Burnt Knob, and Windham High Peak are all mountain peaks located along this 23-mile trail. If you’re looking for things to do near Windham, NY, these trails are just a short distance away.
The panoramic views at Acra Point are worth the effort it takes to reach it!
- Length: 3.4 miles out and back
- Duration: Approximately 2 hours
- Difficulty: Moderately challenging
2. Take Nature Walks on Scenic Paths
Follow The Windham Path for a scenic nature walk along wooded trails, over a covered bridge, and through spacious fields. The gravel path is a 1.5-mile loop and easy enough to walk with your morning coffee in hand. Depending on the season, it’s perfect for spotting fall foliage, wildflowers, and birds and other wildlife.
The Windham Path is a multi-use trail, popular with bikers, runners, and hikers. It’s also a popular snowshoeing and cross-country skiing destination in the winter. To access the trail, park at 4982 Route 23 or 64 NY-296. Part of The Windham Path crosses the property at Hotel Vienna, providing easy access for guests.
You’ll also find a network of hiking and biking trails at the Elm Ridge Trail System, part of the Catskill Preserve Wild Forest. Park at the Route 23 Parking Area and Peck Road Parking Area.
Finally, check out the nature trails at CD Lane Park, Windham’s scenic town park where you’ll also find a lake, playground, and baseball court. If you hit it at the right time, you might just see a couple of resident bald eagles circling over the lake.
3. Take a Chair Lift up Windham Mountain
The primary function of the Skyride at Windham Mountain Resort is to deliver skiers to the slopes in the winter. However, it also runs during the summer and fall, transporting passengers in search of views to the top of Windham Mountain.
The 10-minute ride is incredibly picturesque and once at the top, you’re free to spend as much time as you please. Several picnic tables are available if, like us, you decide to bring a picnic lunch to eat on the mountain top. Restrooms are available.
- Skyride Season: mid-June to mid-October
- Cost: Adults (18 and up): $25. Youth (17 and under): $20.
- Children must be a minimum of 42″ to ride the lift.
4. Zip Down Windham Mountain by Bike
Windham Mountain Bike Park is also located at Windham Mountain. It’s the East Coast’s longest jump trail and welcomes all mountain bikers from beginner to expert. If you’re seeking the adventure of flying down the mountain on two wheels, bike rentals are available.
- Mountain Biking Season: mid-June to mid-October
- Cost: Adults: $59. Youth (17 and under): $49. Season passes are available. Cost of bike rentals vary. See website for details.
5. Scale a Climbing Wall
Try out your rock climbing skills on a 28-foot climbing wall located at the base of the mountain. Minimum age, height, and weight restrictions apply.
- Climbing Wall Season: mid-June to mid-October
- Cost: Two climbs: $15. Unlimited climbs: $30
- See restrictions on age, height, and weight for children
6. Play a Round of Golf at the Windham Country Club
Play 18 holes of golf in the heart of the Catskills at Windham Country Club. Grab a beer and bite to eat afterwards at Mulligan’s Pub. Golfing closes for the season at the end of October.
7. Pamper Yourself at Alpine Spa at Windham Mountain
Treat yourself to a massage at Alpine Spa at Windham Mountain. Reservations by appointment only. Email alpinespa@windhammountain.com
8. Browse the Shops on Main Street in Windham
A small stretch of Route 23 makes up Windham’s quaint Main Street, where you’ll find a selection of restaurants, cafes, and shops, as well as historic homes and the picturesque Windham Public Library.
If you’re busy hiking, mountain biking, or skiing, you might only seek out Windham’s Main Street when you get hungry. However, I do recommend browsing the shops if you have the time, simply to get a sense of the village and, like I did, have a nice conversation or two with the shop owners.
In less than a half-mile radius, you’ll find several unique shops and boutiques.
the Patchwork Co. is housed in a restored 19th century Victorian house and sells a huge selection of fabric, plus anything else you might need for a quilt-making project. Stop at Carole’s Gift Emporium for Windham souvenir T-shirts, as well as a nice selection of soaps, lotions, silk scarves, jewelry, toys, games, and much more. Windham Hardware Store is definitely worth a browse, especially because the building has been there since 1887.
The European Crafts Store specializes in amber jewelry and crafts such as handmade wooden chess sets and shadow boxes. Be sure to pop into Main Street Market if you require any grocery items. There’s also a deli counter where you can grab sandwiches to go.
And don’t miss Windham Fine Arts, a gallery that displays and sells art created by dozens of different artists around the country. Across the street, at the corner of Church and Main, you’ll see the Windham Public Library and just beyond on Church Street, you can catch a movie at the Windham Theater or play an 18-hole game of mini golf.
Windham also hosts numerous special events, including the fall festival known as Windham Autumn Affair. To find out about local festivals, art shows, poetry readings, and more, check out the Main Street Community Center and the Windham Chamber of Commerce ahead of your visit.
9. Sip Wine at The Vineyard at Windham
It’s hard to beat the experience of sampling locally produced wine in a friendly setting, surrounded by rugged Catskill views.
Guests at the Vineyard at Windham can choose from a selection of seating options. In warmer weather, sit on the ground level patio among the vineyard rows or on the elevated deck (my favorite!). When it gets cold, get cozy inside the comfortably rustic tasting room, outfitted with large windows so you don’t miss a moment of those views. Whatever the season, the vineyard should be at the top of your list of things to do in Windham, NY.
Currently, grapes are not grown on-site due to the challenging growing conditions presented by the mountain climate. Grapes are sourced from the Finger Lakes and the North Fork of Long Island. The wine is then made at the Vineyard at Windham.
Order wine by the flight, glass, or bottle. Cheese and meat boards are also available for purchase as a light snack to go with your wine.
- Reservations required
- Open year-round
10. Take a Scenic Drive on Route 23
Driving on Route 23 will reveal some of the most beautiful views in the Catskills. From Main Street in Windham, driving east for eight miles will bring you to the Five State Lookout, where you can park your car and take in views of New Hampshire’s White Mountains, the Green Mountains of Vermont, the Berkshires in Massachusetts, the Catskill and Helderberg Mountains in New York, and the Connecticut Valley.
A leisurely drive in the Catskills can be quick and easy, but the scenic payoff makes it among one of the top things to do in Windham.
11. Dine at the Restaurants in Windham, NY
Hiking the Windham trails can really work up an appetite and luckily, there are lots of dining options to choose from. When planning your meals out, keep in mind that Windham is a small village that attracts a huge number of tourists. That means you should check whether you need reservations, but more importantly, bring patience and kindness along with you.
Also, expect tourist-town prices as opposed to typical Upstate New York prices. With that in mind, read on for cuisine ideas to satisfy every appetite!
Catskill Mountain Country Store & Restaurant
Find an extensive menu of standard breakfast fare like omelets, pancakes, and eggs benedict. It’s also the village general store, where you can stock up on locally made breads, jams, and jellies, plus toys, games, souvenirs, greeting cards, and tons of fun kitschy merchandise.
A large lunch menu is also available. Kids will love the play area outside, complete with a wooden pirate ship. Chickens, goats, and ducks also roam the grounds. 5510 Route 23, Windham, NY
The Windham Local
Choose from an unexpectedly interesting range of lunch items, from pulled pork sandwiches, tuna melts, and mac & cheese to tacos and daily specials that may include Pad Thai, soup dumplings, and mango avocado salad. The comfy industrial chic interior and friendly service adds to the neighborhood vibe. Breakfast is also available. 5410 Route 23, Windham, NY
Millrock Restaurant
Order your favorite hearty Italian dishes including chicken parmesan, linguine and clam sauce, veal piccata, and Frutta di Mare. Pizza is made in a wood-fired oven. 5398 Route 23, Windham, NY
Tap House Grille
As indicated by the name, patrons can choose from lots of local craft beers on tap, as well as wine and signature cocktails. Menu items include burgers, steak, and fish and chips, plus a selection of items less expected from a pub menu, including shrimp tempura, pork buns, and sushi. Check their website for live music performances.
Ze Windham Wine Bar
Enjoy food and wine pairings in an elegant setting on Main Street. 100 different wines from around the world are available, as are cheese and meat plates, food pairings, and a dessert menu.
Windham Pizzeria
This is the restaurant for you if you’re in the mood for New York City-style, brick oven pizza, plus a selection of calzones. Pizza is available by the pie or slice. Gluten-free crust is available.
Babblers Restaurant & Bar
The hearty dishes here are meant to fill you up after a day of outdoor play. Try a traditional fish fry, cheeseburger, chicken & biscuits, and more. Local beers on tap, a nice wine list, and specialty cocktails are on the menu. There’s also an irresistible selection of freshly baked pies for dessert. Adjacent to Babblers is Babbler’s Bakery, which serves coffee, pastries, fresh croissants, and more. Both are located at Wylder Windham Hotel.
Chicken Run Family Restaurant & Steakhouse
St. Louis Style Ribs, ribeye steaks, and fried chicken, all are served with cornbread and two sides on a menu that guarantees customers will not leave hungry. Live music is also on tap weekly. If a casual, fun environment is for you, be sure to eat at Chicken Run at least once. It’s got that down-home local vibe and hearty, no-frills food.
12. Stay at Stylish Windham, NY Hotels
Accommodations in Windham are numerous, though you should still plan to book as early as possible, especially if your visit is during peak fall foliage season. If you’re looking for hotels near Windham Mountain, each lodging option below is less than two miles away.
Wylder Hotel Windham
The Thompson House Resort, established in 1880, provided lodging to Catskills visitors for 140 years until 2021, when Wylder Hotels added Windham to their growing list of U.S. destinations. Guest rooms are housed in seven different historic lodges, and amenities include barrel saunas, hammocks, a pickle ball court, and a heated swimming pool. In the main lodge, guests can cozy up to the fireplace and play a game of backgammon, or play video games, foosball, and more in the basement-level recreation room.
Eastwind Hotel
The décor is a blend of modern, vintage, and Scandinavian design and accommodations include luxury guest rooms and suites, upscale glamping cabins for two, and larger cabins that sleep four. Outdoor barrel saunas and fire pits are among the amenities.
Hotel Vienna
Sprawled across nine acres of scenic countryside, Hotel Vienna provides that tranquil mountain getaway you’re looking for. Guests are welcome to lounge on a common deck or get cozy by a fire pit. The Windham Path can be accessed from the property, so brisk, photo-worthy walks are always awaiting.
Albergo Allegria
A bed and breakfast housed inside a renovated 19th century Queen Anne home offers beautifully decorated rooms and pleasant common areas. Both guests and non-guests are welcome to dine at &Breakfast Restaurant for a selection of gourmet meals prepared with fresh, locally sourced ingredients.
Cave Mountain Motel
A pleasant motel with views of Cave Mountain, which is located just across the street. A continental breakfast is included with your stay.
13. Discover Fun Things to do Near Windham, NY
Windham’s location in the Great Northern Catskills places it within easy proximity to loads of attractions. Ten miles to the south, Hunter Mountain offers a wide range of fall activities including sky rides, 4×4 off-road adventures, hiking, and zip lining. Like Windham Mountain, Hunter is popular in the fall, and then transforms into a major Catskills skiing destination in the winter.
Want to see the tallest two-tier waterfall in the Empire State? Head 18 miles south of Windham to Kaaterskill Falls, where you can view the upper falls from an observation platform, hike down to the lower portion of the falls, or find trailheads to more scenic hikes in The Catskills.
From Windham, head east toward the Hudson River for about 30 miles and you’ll find yourself in the charming town of Catskill, where you can visit the historic home of Thomas Cole, the founder of the Hudson River Art School movement.
How to Get to Windham
As with most small towns in Upstate New York, driving is the most convenient option. Approximate driving distance and time from major cities:
- Hudson: 30 miles (48 km). 40 minutes.
- Albany: 55 miles (88 km). 1 hour.
- New York City: 145 miles (235 km). 2.5 hours.
- Montreal: 275 miles (443 km). 4.5 hours.
Additional ways to travel to Windham:
- By bus: Greyhound and Trailways make stops in Windham from select origin points.
- By train: The closest Amtrak train station is in Hudson, NY.
- By air: The closest major airport is in Albany, NY.
