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

Union Chapel, Mill Rd. Windham NY. Wikimedia Commons / Kenneth C. Zirkel

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 summer months, as well, with everything from outdoor adventures to wine tastings, spa treatments, and fine French 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! Just be sure to check in with area businesses beforehand to confirm their COVID-19 policies and have the best #shoplocal experience possible.

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 housemade mozzarella.

5510 Rte 23, Windham

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 BMXers blasting up and down the rocky slopesides.


We’re just gonna leave this here because #heatwave

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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 Snow Bird Ski Shop and Charlie’s Windham Mountain Ski Shop or drop by Windham Fine Arts for seasonal exhibitions of contemporary artists working in diverse media.

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 local music on summer nights.

5410 Main St, Windham

2 p.m. – Relax at The Windham Spa

This state-of-the-art spa offers mani-pedis from $65, with more complex treatments involving hot stones, palo santo, and grapefruit, as well as a variety of massages and hair removal services for those who really need to unwind. Anyone looking to try something new can opt for the “R&R Facial,” which incorporates microdermabrasion, a double peel facial, and LED lights.

16 Mitchell Hollow Rd, Windham

What makes a great wine bar? Tasteful decor? 40 bottles by the glass? carefully curated selection? Home made food to pair? What if it’s all of those things plus an owner so passionate about wine she brought out 7 of her favorite bottles and blind tasted with you? That would make the best wine bar I’ve been to anywhere in recent years. Cordelia, owner of @zewindhamwinebar , was incredibly generous with her wine offerings, as well as her time and knowledge – taking me on a journey from Cru Beaujolais to mini Super Tuscan, to Rioja Crianza, to Austrian Reds like Blaufränkisch. Out of the 7, I got 2, @frankdrinkswine would be proud:) The most difficult ones were Austrian reds and blends. We finished with this Châteauneuf-du-pape: the heat & alcohol gave away a warm-climate region. Berries and cherries on the nose. Good structure, med body, med acidity, smooth tannin and a dense finish. Under Cordelia’s guidance, I eventually got there:) What a fun, unexpected night, a true gem in Upstate New York. Next time Cordelia, I’ll bring the bottle😉

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

Acclaimed for its vast selection — over 40 vintages — and friendly staff, Ze is the place to go for vino lovers who want to learn while they sip. This winter, enter the Scandanavian-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.

5369 Main St, Windham

7 p.m. – Savor French fare at Bistro Brie & Bordeaux

This is it: a real-deal, old-country French bistro. The Lyon-trained Stéphane Desgaches transformed a historic 1875 building into a house of serious cuisine in the Hudson Valley, stacking his dinner-only menu with classics like escargot and filet mignon, as well as risotto, linguine, and puff pastry. And for vino aficionados, Bistro Brie & Bordeaux takes its cuisine to the next level with a curated, imported wine list.

5386 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, queen and king beds, and “picnic-styled” to-go breakfast with locally-sourced ingredients from Hudson Valley-area farms and roasters. Availability is heavily dependent on the season.


Related: This Is How to Spend 24 Hours in Newburgh