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

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


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Union Chapel, Mill Rd. Windham NY, dates back to 1897 and is on the National Register of Historic Places.

Wikimedia Commons / Kenneth C. Zirkel

 

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.

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 housemade mozzarella.

5510 Rte 23, Windham
518.734.3387
Mon-Thurs 9 a.m. – 5 p.m., Fri 9 a.m. – 6 p.m., Sat 8 a.m. – 6 p.m., Sun 8 a.m. – 5 p.m.

 

 

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.

Windham

 

 
 
 
 
 
 
 
 
 
 
 
 
 

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 ginger squash soup. It's a great refill option that also hosts local music on summer nights.

5410 Main St, Windham
518.750.8300
Sun-Thurs 7 a.m. – 5 p.m., Fri 7 a.m. – 9 p.m., Sat 7 a.m. – 7 p.m.

 

 

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 “Shortwave Facial,” which incorporates radio frequencies, LED lights, and an Arctic Berry Triple Peel.

16 Mitchell Hollow Rd, Windham
518.734.9617
Thurs-Sat 10 a.m. – 6 p.m., Sun-Mon 10 a.m. – 5 p.m., closed Tues-Wed

 

 
 
 
 
 
 
 
 
 
 
 
 
 

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. The bar pairs its wine with small plates of mozzarella, salmon, and charcuterie, with vegan options by request. If visiting on a Tuesday, guests can sign up for the special Wine School, which offers in-depth instruction based around a weekly theme.

5369 Main St, Windham
518.734.9200
Hours vary by season

 

 

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

This is it: a real-deal, Zagat-rated, old-country French bistro. The Lyon-trained Stéphane Desgaches transformed a historic 1875 building into a house of serious cuisine, 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
518.734.4911
Hours vary by season

 

 
 
 
 
 
 
 
 
 
 
 
 
 

Your next getaway is just a phone call away: (518) 734-5560 #getaway #localhotels

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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 free breakfast with locally-sourced ingredients from area farms and roasters.

Rooms start at $99, with availability heavily dependent on the season.

Windham
518.734.5560


Related: This Is How to Spend 24 Hours in Newburgh

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