What to Do in Windham: A 24-Hour Guide to the Greene County Retreat

The Hudson Valley's dreamy resort town tempts with pristine slopes, chic shops, and farm-to-table dining at every corner.

With its prestige resort and expansive set of trails, Windham is beloved by skiers, snowboarders, and outdoor fiends in the Hudson Valley and beyond. The Greene County town has quite a lot to do during the warmer months as well, with everything from outdoor adventures to wine tastings, spa treatments, and fine Italian cuisine available.

Here’s your guide to an ideal 24 hours in this bucolic mountain town. If you go, tag us @HudsonValleyMag on Instagram with your favorite destinations!

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9 a.m. – Eat local at Catskill Mountain Country Store

This classic diner spot includes heaping helpings of buttermilk pancakes, Belgian waffles, and French toast, as well as a creative menu of omelets made from free-range organic eggs, local produce, and house-made mozzarella. When you’re done eating, check out the store’s range of products from apparel to games.

5510 Rte 23, Windham


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10 a.m. – Take a nature walk at Elm Ridge Wild Forest

Elm Ridge serves as the trailhead for Windham High Peak, but its lower reaches are honeycombed with trails for those looking for a somewhat less strenuous stroll. This area is also a favorite of off-road cyclists, so watch out for mountain bikers blasting up and down the rocky slopesides.



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11:30 a.m. – Browse the shops in town

With knickknacks galore, Windham’s shops are a delight for visitors to the region and Hudson Valleyites alike. Lovers of the great outdoors can shop off-season ski stuff at Windham Mountain Outfitters and, while you’re over there, stop by Briars and Brambles Books for reads on Hudson Valley landmarks or history. If you’re gift shopping, What the Soap has you covered for homemade soaps, body scrubs, or moisturizers, and The Patchwork Co. is a unique shop with hundreds of fabrics to browse for making your own quilts. When you crave a mid-morning sweet treat, head to Babblers Bakery right down the road at the Wylder Windham, or drop by Windham Fine Arts for seasonal exhibitions of contemporary artists working in diverse media.


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12:30 p.m. – Lunch it up at The Windham Local

This community-focused restaurant trumpets its fresh produce from local farms, focusing on sandwiches and wraps that balance rich options like truffle grilled cheese and pulled pork with salads and a classic tomato soup. It’s a great refill option that also hosts live music from local musicians every Friday and Saturday.

5410 Main St, Windham


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2 p.m. – Relax at The Windham Spa

This state-of-the-art spa offers facials starting at $120, with more complex treatments involving hot stones, cupping, and aromatherapy, as well as a variety of massages and skincare services for those who really need to unwind. Anyone looking to try something new can opt for the “The Organic Goddess (The O.G.),” which incorporates microdermabrasion, an organic bright eyes peel, and a radio frequency treatment.

16 Mitchell Hollow Rd, Windham


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5 p.m. – Taste all the wine and cheese at Ze Windham Wine Bar

Acclaimed for its vast selection — over 100 different wines from around the world — and friendly staff, Ze is the place to go for vino lovers who want to learn while they sip. This winter, enter the Swedish-German-style outdoor garden and cozy up around the fire pits to sip on wine from around the world, hot mulled wine, or specialty beer. When it’s time to dine, the bar serves up soups, cheese and charcuterie plates, and fireside Alpine s’mores. 

5369 Main St, Windham

7 p.m. – Savor Italian fare at Millrock Restaurant

Millrock serves up delicious Italian fare in its lively restaurant inspired by Italian traditions and rustic American roots. Operating since 1996, Millrock prides itself on hearty portions of pasta, fresh seafood, and savory cuts of meats, alongside a brimming wine list in a cozy atmosphere. Enjoy views of the surrounding area while indulging in stuffed rigatoni a la vodka, rosemary chicken, or eggplant parmesan. Don’t skip the crème brulee or the lemon cello flute for dessert.

5398 Rte 23, Windham

9:30 p.m. – Stay the night at Albergo Allegria Bed & Breakfast

Albergo Allegria has two locations: a four-suite cabin on Main Street and the inn just outside of town. This Trip Advisor-endorsed B&B has well-appointed rooms for two or more with private baths and queen and king sized beds. Breakfast is salty or sweet with baked eggs, Belgian waffles, and fresh baked muffins, all made with locally-sourced ingredients from Hudson Valley-area farms and roasters. 



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Related: Coxsackie Day Trip: How to Plan a Perfect 24 Hours in Town

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