Have you been to Woodstock, NY?
If you haven’t, I’m guessing you’ve at least heard about this small Catskills town in upstate NY because of the famous 1969 music festival with the same name.
Interestingly enough, the Woodstock Rock festival actually took place on a dairy farm, 40 miles away from the town. And the name came from the investment group, “Woodstock Ventures” which backed the concert.
None the less, the town of Woodstock has a bit of that hippie vibe you surely would have found at the festival. Add to that curated shops you’d expect to find in Brooklyn, Scandinavian-influenced coffee shops and casual cafes churning out NYC caliber food, and you have modern-day Woodstock, a picturesque and trendy town in the Catskills.
I’ve visited Woodstock and the surrounding area a few times over the years, but this is the first time I’ve visited during the winter. While we spent a lot of time drinking wine by the fire, we also managed to do some exploring and realized there’s plenty to see and do in Woodstock NY in the wintertime.
Now that I’m back, I figured it was time to spill the goods.
Hence, the Woodstock NY winter travel guide!
Keep reading to find out everything there is to do and see in and around Woodstock in the wintertime.
Oh, and if you want to know where to eat, drink and get the best coffee in Woodstock, check out my Woodstock food guide.
A note about the COVID-19 Pandemic: Please note that all of the accommodations and companies running activities I list in this guide have taken measures to ensure everyone’s safety during the pandemic. However, with guidelines changing constantly, please check online before visiting any facilities to know what the exact COVID-19 protocols are and to confirm that they are open.
The Woodstock, NY Winter Travel Guide
The chef’s kitchen at the Airbnb where we stayed in Woodstock
Where to Stay in Woodstock, NY
Hotel Dylan – a music-themed, boutique hotel with bohemian designed rooms, 3 miles away from town and close to popular hiking spots.
Woodstock Way Hotel – a design-minded wellness-escape, with individual cabins, some boasting large kitchens, and common areas. They offer private yoga lessons, massages, and spiritual healing sessions. The larger cabins are a great option for families and the hotel is a short walk into the heart of town.
The Woodstock Inn on the Millstream – a classic B&B stay, with bright rooms furnished with antiques or larger cabins and cottages with fireplaces, private balconies, and hot tubs.
The Herwood Inn – a boutique inn located in the heart of Woodstock with 4 bohemian designed suites, all with kitchenettes and seating areas. Two of the suites are pet friendly.
Twin Gables of Woodstock – Right in the center of town, this private home was turned into a boutique hotel in 1926, and revived in 2020 with kitschy, colorful décor, offering suites with private bathrooms and a guest house with shared accommodations.
Airbnb – Another option – possibly preferable during the COVID-19 pandemic – is renting a house. There are plenty of options on Airbnb and also VRBO.
Outdoor Activities to Do in Woodstock NY in Winter
We enjoyed walking the recently open Ashokan Rail Trail. *Masks were off just for this photo!
Hiking – This is a year-round activity in the Catskills. Check out the new Ashokan Rail Trail or hike up Overlook Mountain for incredible views. You can also do some great hiking at Wittenberg Mountain and Slide Mountain.
Skiing – There are two good mountains to ski nearby, Windham and Belleayre. Both are smaller and less crowded than Hunter Mountain. Some hotels offer discount tickets if you are a guest, so ask before buying your tickets.
Cross Country Skiing & Snow Shoeing – For an exhilarating and fun outdoor experience, try snowshoeing or cross country skiing. You can do both at the Mountain Trails Cross Country Ski Center in Tannersville, 19 miles from Woodstock. (As of when I wrote this guide, the center is closed due to staffing issues because of the pandemic. Check their website for the most up to date info on when they will reopen.) You can also try out snowshoeing and cross country skiing at the Frost Valley YMCA in Claryville, 36 miles away. (Right now they are only offering cross country skiing to overnight guests, due to the pandemic.)
Snowmobiling – Dash through the snow on an interconnected network of back-country trails. The best place to rent snowmobiles and a guided tour, head to Rip Van Winkle Ranch in Haines Falls, about 16 miles away from Woodstock.
Cultural Activities in Woodstock, NY
Waterfall Way, next to the Center for Photography
The Center for Photography – a museum promoting contemporary photography. The center is open now but you need to make an appointment to visit.
The Tibetan Monastery – Unfortunately, the center is closed right now due to COVID-19, but when it reopens, you can take a guided tour here, shop in their bookstore, or walk the sculptural trail at Opus 40. In the meantime, they are offering many teachings and lectures online.
Zen Mountain Monastery – Also closed right now due to COVID-19, but normally offering Sunday morning and Wednesday evening Zazen (zen meditation) that are open to the public.
Art Galleries – there are a few other art galleries and museums worth a visit: Woodstock Artists Association and Museum, the Woodstock Byrdcliffe Guild, and the Elena Zang Gallery.
Where to Shop in Woodstock, NY
The shop Three Turtle Doves is full of great vintage finds
Candlestick – for every kind of candle you could ever imagine. I never walk out of this store without buying at least a couple of candles!
The Golden Notebook – I love supporting local, independent bookstores and Woodstock has a good one.
Shop Little House – a small store with highly curated objects and furniture for your home
Three Turtle Doves – my girlfriends and I could easily spend all day in this store trying on vintage dresses, jewelry and shoes. The store also has a great handbag collection.
Headstock & Co. – For Woodstock memorabilia, handcrafted waterpipes, novelty items, and more, check out this shop.
Curious to know more about Woodstock’s culinary offerings? Check out my full blog post about where to eat and drink in Woodstock, NY.
Pro Travel Tip: Need a bathroom while you’re walking through town? There are clean, public restrooms located in Town Hall.
Are you Ready to Plan a Winter Trip to Woodstock NY?
I hope this post has inspired you to plan a winter weekend in Woodstock, NY. I know that I can’t wait to go back!
Don’t forget to also check out my Woodstock, NY Food guide which has a comprehensive list of the best restaurants in the area.
Also, make sure to bookmark my other posts about Upstate NY:
Safe places to stay in the Catskills during COVID-19
A weekend Itinerary for Livingston Manor, in the Catskills
Hotel Guide: Antrim Streamside in Livingston Manor
Weekend Roadtrip to the Catskills Mountains
Happy travels!
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