Home Food + DrinkCoffee Weekend Getaway Guide to Woodstock, NY

Weekend Getaway Guide to Woodstock, NY

by Lauren Alberti
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Weekend getaways are not just for summertime. A winter weekend out of town can be therapeutic, relaxing, and extremely necessary. Taking a moment to get a change of scenery (and a change in rhythm) can help beat the winter blues and break up the monotony of the bitter cold months. Woodstock, New York is a great option, regardless of the time of year. The town is known for its groovy vibes that take inspiration from the Summer of Love’s 1969 Woodstock Music and Arts Festival. While those iconic three days of music actually took place in Bethel, NY, which is not within Woodstock’s town limits, entering Woodstock is like entering another decade. Peace signs riddle the streets, tie-dye clothes are available for purchase, and vinyl records are still being played. The small-town feel is tangible, and the locals seem to welcome visitors with open arms. Though the drive is just over two hours from Hoboken, visiting Woodstock, NY feels like being transported far, far away from city life. Read on for our guide to all things Woodstock, New York.

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Where to Stay

Woodstock Way Hotel | 10 Waterfall Way

woodstock way new york

Just steps away from Tinker Street — where all the action happens — Woodstock Way Hotel is perched right next to a gorgeous waterfall and has fire pits and Adirondack chairs set up for guests to enjoy the scenery — regardless of the season. The rooms are uniquely and artfully decorated, making for a fun stay.

Read More: How to Have a Day in Cold Spring, New York

The Woodstock Inn on the Millstream | 48 Tannery Brook Road

woodstock inn millstream

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Located on the picturesque Millstream, The Woodstock Inn is a great option for anyone looking to stay nearby town but off the main street. The inn has different rooming options, depending on price point and necessities. There are motel-style rooms available, in addition to more luxurious Deluxe Rooms and private cottages. Deluxe rooms and cottages all have electric fireplaces that really set the mood for a cozy weekend upstate.

Twin Gables | 73 Tinker Street


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This bed and breakfast is located right on Tinker Street, and is housed in an 1880s private home. The hotel is designed by artists for artists, and every corner is decorated to encourage creativity. There is even an open studio available to guests in the attic space.

The Herwood Inn | 148 Tinker Street


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This groovy boutique hotel is trendy and exciting, with room options for groups of two to four people +  some accommodate furry friends, as well. Most importantly, this inn has a beautiful outdoor hot tub, allowing optimal rest and relaxation on your weekend getaway.

Where to Eat

silvia woodstock

^ Silvia

There are so many great places to eat in this small town, it’s almost impossible to include them all. Starting with breakfast, one of the stand-out spots is Oriole 9, the town’s staple diner-esque restaurant. Grabbing a coffee and a pastry from Bread Alone Bakery is also a must. Lunch and dinner have several great options ready for you, including Yum Yum Noodle Bar, Tinker Taco Lab, Mud Club, and Garden Cafe — a spot where you can get vegan and vegetarian food. A trip to Woodstock is not complete without a fancy night out at either Silvia or Cucina — or both! These two highly-rated restaurants have top-tier menus and the perfect vibe for a cozy dinner next to a fireplace on a cold winter night.

Things to Do + See

Tinker Street

candlestock woodstock

^ Candlestock

The main street in Woodstock is Tinker Street, which is lined with adorable mom-and-pop shops to spend the day exploring. Weaving through antique stores, gift shops, herb shops, apothecaries, cafes, and bakeries before grabbing lunch or dinner in town is a perfect afternoon spent. You can pick up a unique candle from Candlestock, find a new winter read at The Golden Notebook, try on some authentic vintage clothing at Rock City Vintage, and shop at some of the numerous boutiques, including Lily’s and Woodstock Trading Post.


There’s plenty of hiking in Woodstock. Check out Overlook Mountain or the Shawangunk Mountains for gorgeous mountain views of the Hudson Valley.

Visit the Tibetan Monastery

Yes, there’s a Buddhist Tibetan Monastery right in Woodstock. Karma Triyana Dharmachakra is the first Karma Kagyu monastery to be established in the United States. It is located on top of a small mountain and is open to the public. Read more about the Monastery here.

Get Pampered

glo spa woodstock

^ Glo Spa

There are a few spas to check out while visiting Woodstock. Glo Spa offers luxurious spa treatments that won’t break the bank, in addition to fitness classes on premises. Their shop is full of skincare products to try out, and their staff is welcoming and will help you find exactly what you need.

See More: 15 Northeast Airbnbs You Need to Book ASAP

See Some Music

In the warmer months, Woodstock is filled with live outdoor music seemingly around every corner. When it’s a bit more chilly out, there is still music to be heard. The Bearsville Theater hosts live indie bands and Levon Helm Studios typically has an exciting act to see. Colony is a music venue that dates all the way back to 1929. The Woodstock Playhouse is also a great place to catch some live theater.

No matter what you are looking for in a getaway — whether it’s rest and relaxation or getting outside and being active — Woodstock, NY has what you need. It’s a quick drive up the NYS Thruway from Hudson County, and is a completely walkable town. Time to set that OOO email response and have the upstate vacation you deserve.

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