Looking for things to do in Windham? You’re in the right place. Windham, NY is a lively Catskills town with year-round appeal. It has beloved ski slopes and mountain biking trails, cozy restaurants, great shops, and plenty of fresh mountain air.
Sometimes called the “Gem of the Catskills”, Windham is one of the region’s most popular bases for outdoor adventure. You’ve got easy access to great hiking trails, waterfalls, and scenic drives. It’s also got the right mix of small-town charm and activity; it has more bustle than some nearby hamlets, but it’s still pretty chill.
Here’s a roundup of places to visit in, around, and near Windham. You’ll find outdoor activities, cultural spots, places to eat and drink, and local stops worth checking out.
Lots to do in Windham
On your way into Windham — if you’re driving from the east on Route 23 — pull into the Five State Lookout parking area where you can look out over the enormous flats of the Hudson Valley floor to see distant mountains in NY, NH, MA, VT, and CT.
Wine enthusiasts can hit The Vineyard at Windham.
Fans of contemporary art should check out Windham Fine Arts.
And, of course, the big draw for skiers and snowboarders is Windham Mountain Club, just off South Street.
Best Places to Eat in Windham
Clutch & Throttle Cookies
A sweet coffee shop on with strong espresso and delicious egg-and-bacon-croissants. Perfect if you’re looking for a quick jolt or a place to linger with a laptop.
Higher Grounds Coffee Co.
A cozy café on South Street with great coffee, pastries, and breakfast bites. Great for grabbing a cappuccino before hitting the trails, or a warm-up after skiing.
The Windham Local
A great cafe with quality fare — and it’s the only place locally to grab some Thai and dim sum bites.
Millrock Restaurant & Bar
A lively restaurant that combines Italian traditions with rustic American roots.
Babblers at the Thompson House
As a restaurant, bar and bakery, Babblers has you covered for all the good stuff.
Shopping in Windham
Briars & Brambles Books
Fantastic indie bookshop close to Higher Grounds that stocks quality reads.
Catskill Mountain Country Store
Part store, part bakery, part garden center, part restaurant. Browse local crafts, baked goods, jams, and gifts, or wander their small outdoor paths and petting area.
Maplecrest Valley Apiary
A local honey producer with hives across the Windham area. They sell pure raw honey sourced from wildflower meadows and organic farmland.
Olivia’s Wine & Spirits
A curated wine and spirits shop with a personal touch. They focus on interesting bottles and offer guidance if you’re stocking up for a weekend stay.
Windham Wine & Liquors
A well-stocked local liquor store with monthly tastings and gift baskets. They offer case discounts and delivery for events.
The Play Den
A charming children’s toy boutique offering quality toys, books, clothing, and furniture for newborns through age 12. Small toys come in bundles for easy gifting.
Carole’s Gift Emporium
A welcoming, long-running gift shop with jewelry, candles, toys, accessories, and classic Catskills souvenirs. Great for browsing and picking up affordable gifts.
European Craft Store
A cozy shop offering handmade woodcrafts, chess sets, pottery, amber jewelry, and ornate holiday ornaments. They also do custom woodworking and have been a Windham staple for decades.
Garden of Stone
A unique garden and home décor shop specializing in hand-cast concrete pieces like statues, birdbaths, planters, and gnomes. Fresh-cut flowers round out the selection.
Miss Minnie’s Makins & More
A home-grown shop offering handcrafted gifts, Catskills souvenirs, custom mugs and shirts, and artisanal appetizer/dessert boards. They also make beautiful focaccia breads.
The Patchwork Company
A beloved quilting shop packed with colorful fabrics, patterns, and quilting supplies. Friendly staff and a curated selection make it a popular stop for fiber artists.
The Knitting Room
A warm, welcoming yarn shop carrying indie-dyed yarns, handcrafted garments, and sustainable wool goods. Visitors are invited to knit, crochet, or just hang out.
Gerhards Guitarworks
A full-service custom guitar workshop offering handcrafted instruments, expert repairs, and vintage restorations. Their showroom features beautiful builds and rare finds.
Best Hikes & Trails Near Windham, NY
Easy Hikes Near Windham
The Windham Path is a gentle, scenic, family-friendly loop just outside town, perfect for walkers, runners, cyclists, and anyone who wants an easy dose of Catskills beauty. The full loop is a little over 1.5 miles and winds through open meadows, over wooden bridges, and along peaceful stretches of the Batavia Kill.
It’s flat, wide, and beautifully maintained. In summer it’s great for a casual stroll or a mellow bike ride. In fall you get long views of Windham Mountain framed by peak foliage. In winter it turns into a quiet spot for walking or cross-country skiing.
Parking is easy and the vibe is relaxed. If you want something low-key and outdoorsy near Main Street, the Windham Path is one of the best quick hits in town.
Mountain Hikes Near Windham
There are so many incredible mountain hikes right in Windham and close by. For starters, there’s Windham High Peak which you can access from Route 23. It’s one of the Catskills’ thirty-five highest peaks, and one of the easiest of the high peaks to hike, with banger views from the summit.
Close by is the Blackhead Range, which combines some of the finest scenic views and most challenging terrain we have in the Catskills.
Looking to find the perfect Catskills hike for your ability-level? Try the New York Hike Finder.
BTW, if you want the best Catskills hiking content, follow my @TotalCatskills account.
Mountain Biking Trails Near Windham
Whether you’re looking to explore wooded hillsides, get in a serious cardio session, or just cruise through nature, there are several excellent trail systems within a short drive.
Apart from easy-cycling around The Windham Path, there’s…
Elm Ridge Trail System (Windham, NY)
Just 3 minutes east on Route 23, you’ll find the trailhead for Windham High Peak and the Elm Ridge Wild Forest, home to one of the best mountain biking trail networks in the Catskills.
Maintained in part by the Windham Area Recreation Foundation (WARF), the Elm Ridge trail system includes technical climbs, fast descents, and scenic ridge rides through classic Catskill forest.
Elm Ridge is a go-to spot for both casual riders and serious mountain bikers, with trail options ranging from flowy, machine-built segments to more rugged backcountry routes.
Roundtopia (Round Top Trail Network)
About 20 minutes east of Windham, the Round Top Trail Network features over 20 miles of mountain biking trails carved into privately owned land but generously opened to the public.
Often referred to as “Roundtopia”, this interconnected system offers a mix of single-track, double-track, and fire roads, with options for both beginners and more experienced riders. In the winter months, many of the trails are groomed for fat biking, making it a true year-round destination.
Public access is available via multiple local landmarks and resorts, including:
- Riedlbauer’s Resort
- Glen Falls House
- Winter Clove Inn
- Crystal Brook Resort
- Mountain Brauhaus
Each entrance offers a slightly different entry point into the network, and some locations feature trail signage and bike-friendly amenities. The atmosphere is relaxed and community-driven — a local gem for anyone looking to ride without the crowds.
More…
I hope you found this round-up of things to do in Windham helpful. Check out this list of amazing places to stay.
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