top of page

Where to Eat & Stay in Woodstock, NY

Contrary to popular belief the Woodstock of 1969 was not held in Woodstock, NY (it was held in Bethel, NY) although it could have easily been held in this hippy, tie-dyed-wearing, free-loving community comprised of many Manhattenites who escape the demands of the city for a tranquil respite in the country. Our family tradition, when we lived in New York City, was to visit Woodstock each Columbus Day weekend when foliage was at its peak and the temperatures were not too frigid. I was thrilled to make a visit again on Columbus Day weekend reliving some wonderful memories. You'll love strolling along Tinker Street and shopping in the eclectic shops, dropping into a great yoga session at Euphoria Yoga, and eating at any of the many delicious restaurants in town. During the summer, there are weekly community drumming sessions (which inspired my drum circles in La Jolla). This easy-going, super casual destination makes for an easy weekend getaway when you next visit Manhattan. I personally highly recommend making a visit for two nights.

Located right off Tinker Street the location of this hotel cannot be beat. The rooms are large and pristine and the hotel offers complimentary coffee each morning in their lobby along with stocked firepits at dusk.

pros: great location, well-designed and spacious rooms, a stocked fridge with complimentary artisanal sodas

cons: a bit pricey compared to other options in the area, especially since it misses details that should be provided at this price point,like robes and umbrellas (it rains a lot in the area and rained while we were in town)

A visit to Cucina when in Woodstock is mandatory in our family. We have eaten here dozens of times over the years and love it every single time. The large space is always packed with patrons and consistently carries the scent of wood-fired pizzas. It's elegant, yet cozy, and the Italian recipes are always delicious.

pros: great food, attentive service, warm and inviting atmosphere, all pasta options can be made gluten-free

cons: reservations are required

must order: penne puttanesca with olives, capers, garlic, parsley, spicy tomato, and any of the pizzas

An old train station has been converted into a laid-back, open-aired bar with live music, a pool table, and light food options. It's a super casual spot to meet with friends for pre or post-dinner drinks.

pros: casual, unpretentious, fun outdoor space

cons: a little grungy

must have: there isn't anything you must have here except for a good time

Even on an extremely rainy day, visitors lined up to eat a delicious breakfast at this popular eatery. Although they are open all day, serving three meals, I find that breakfast is their forte.

pros: lively, great breakfast options, bustling environment

cons: if you don't make a reservation in advance, wait times can be long

must order: fried cauliflower wings and huevos rancheros

This bakery pumps out baked goods, using only organic wheat, all morning long. People flock to get freshly baked bread and pastries early in the morning. I love starting my day here with a great cup of coffee and a flakey croissant to go with it. I am not one to ever wait in lines, but I do here.

pros: delicious organic, wood-fired breads and homemade pastries

cons: long lines, although they move quickly

must order: almond croissant and any of the artisan breads

Woodfired bagels. Disco balls. Firepits. Fairies. Expansive garden seating. This place is awesome.

pros: one of the coolest bagel shops you'll ever eat in, on Fridays and Saturdays they make wood-fired sourdough pizzas until 8:00 pm

cons: no indoor seating

must order: green eggs & ham bagel (I got mine minus the ham): fried egg, spinach, cheddar cheese and sauteed garlic

Half market/half restaurant, Sunfrost is a local's favorite, especially during summer when the patio opens onto the picnic table-lined grass field. I have always loved this joint for takeout - especially for a burrito with rice, beans, and cheese.

pros: while you wait for your order you can conveniently get some grocery shopping done, a simple menu with organic, healthy ingredients

cons: have them repeat your order as they often make mistakes

must order: a customized smoothie made just the way you love it along with a burrito

A New York stuffed bagel! Why hasn't anyone thought of this yet? Choose your favorite combination, which changes regularly, but mostly always offered favorites like Ruben stuffed bagels, buffalo chicken stuffed bagels, and BBQ tempeh stuffed bagels. The bagels are made onsite in this quaint little eatery with helpful staff who will help guide you in the decision-making process.

pros: unique concept, interesting options to choose from, friendly staff, traditional bagels are available too for the less adventurous bagel eater

cons: just a few seats are available along the window must order: egg and cheese stuffed everything bagel with locally sourced eggs and the pizza bagel

The owners of this artisanal chocolate shop met while working at Per Se, a three-Michelin-starred restaurant in New York City. Located in the heart of the village, you won't miss the opportunity to buy some delicious hand-crafted confections that are packaged beautifully.

pros: extremely attractive, and perfectly made chocolates

cons: a bit pricey

must have: the peanut butter and jelly, the dark chocolate, and the salted caramel truffles


bottom of page