Woodstock NY: Things to do, Where to Stay & What to Eat

So you’re planning a trip to Woodstock, NY? You might be wondering the best things to do in Woodstock are, or where to stay, or even where to eat. This guide will cover it all!

things to do in woodstock ny

Located in the heart of the Catskill Forest Preserve, Woodstock NY is both a natural phenomenon and home to a great number of artists. If you’re visiting Woodstock, NY and you’re looking fo all the best things to do in Woodstock, then this is the best guide for you!

This welcoming little village not only boasts beautiful scenery and some of the best trails around, but offers excellent restaurants, cultural outings and quaint hidden gems. Keep reading to learn everything you need to know about Woodstock NY!

Things to do in Woodstock NY

So, you’re planning a visit to Woodstock NY, and you might be looking for ideas on things to do in Woodstock NY! Hopefully this list will give you lots of ideas and inspiration for your visit to Woodstock NY! Here are 10 things to do in Woodstock NY…

Overlook Mountain

First on my list of things to do in Woodstock NY, it’s Overlook mountain. Arguably the central point of Woodstock, NY, Overlook Mountain is home to one of the five remaining Catskill Mountain fire towers. Constructed to prevent and control fires in the region between 1908 and 1950, the towers now act as an interesting ode to Woodstock’s history. 

As they’re now disused, visitors can explore the area on a 9-mile hiking trail that winds all the way around the mountain. Make sure to pack your hiking boots for this one, as it’s quite the trek! Definitely a must-do on this list of things to do in Woodstock NY.

things to do in woodstock new york

Karma Triyana Dharmachakra Tibetan Buddhist Monestery

Karma Triyana Dharmachakra is my next idea for things to do in Woodstock NY. This is a Tibetan Monastery that’s located just above Woodstock. Offering numerous teaching workshops and classes in traditional Tibetan Buddhism, it’s a great guided tour and exploration into one of the world’s most peaceful religions. Weekend programs are held every weekend as well, so there’s plenty to do here!

If you’re looking to expand your cultural horizons, then this is a fantastic option for things to do in Woodstock NY.

list of things to do in woodstock new york

World’s Largest Kaleidoscope

Though it’s perhaps a strange feature of Woodstock, the area just so happens to be home to the World’s Largest Kaleidoscope! Located at the Emerson Resort & Spa, for $10, you can watch a ten-minute show in the refurbished farm accompanied by some cool sound and music. Not only that, but they even have a bunch of gift shops that you can explore, with puzzles, kaleidoscopes (of course) and plush toys that kids love. This is a great idea for things to do in Woodstock NY, especially for families!

Mowers Saturday Flea Market

Everyone loves a Saturday market – which is why this makes my list of things to do in Woodstock NY! Mower’s Saturday Market has been a staple in Woodstock for years, and it’s easy to see why. A family-owned and operated market that’s held every Saturday (and Sunday!) in a grass-covered field, it’s a real gem.

Vendors sell fresh farm goods, fruits, vegetables, handmade goods, art and much more. If you love a good flea market or farmer’s market, this one is the perfect amalgamation of both. So, head down to Maple Lane and try to snag some bargains…If you love shopping this is a must-do for things to do in Woodstock NY.

best things to do in woodstock ny

Shawangunk Mountains

Next on my list of things to do in Woodstock NY, it’s the Shawangunk Mountains. The Shawangunk Mountains are comprised of bedrock that spans from New Jersey to the Catskill Mountains through Ulster, Sullivan and Orange Countries. A popular outdoor recreation venue for mountain climbers and wildlife enthusiasts, it’s a true testament to the power of the Great Outdoors.

With more than 100 miles of hiking trails, the area is teeming with beautiful scenery and unique wildlife. As it’s a designated Nature Conservancy area, it also offers a range of educational conservation programs. If the weather is on your side, this is a truly fantastic day out.

Go shopping on Tinker Street

Tinker Street near Mill Hill Road is the heart of quirky independent shops in Woodstock. You’ll find all these lovely stores near the village green and it’s a gorgeous place to stroll through tree-lined streets and pop in and out of unique boutiques selling all kinds of items.

things to do in woodstock

Get pampered at River Rock Health Spa

Who doesn’t love a good pamper? Next on my list of things to do in Woodstock NY, it’s a spa day! A luxurious spa in the centre of Woodstock, the River Rock Health Spa is a tranquil escape from the madness of the city. With a range of services that include massages, skin care, pedicures and more, it’s the perfect getaway for stressed out city workers.

What makes this place special is that they also offer alternative treatments. If you’ve ever wanted to try intuitive kinesiology or aura photography, this is a great place to give it a go!

Sunfrost Farm

Sunfrost Farm is my next idea on my list of things to do in Woodstock NY. Sunfrost Farm is the Hudson Valley’s leading retailer for local and organic produce. With amazing fresh food on offer, you can spend a good hour here looking at everything that’s on offer. Visitors to the farm can enjoy home-cooked meals from various vendors, with everything from fresh sandwiches to indulgent desserts.

The thick ice cream shakes here are a major hit amongst locals as they’re just that good! There’s also a cafe there too for sampling some of these delicious foods! Oh, and if you visit Sunfrost Farm in the autumn (around Halloween) be sure to visit, they put on quite a show!

things to do in woodstock ny

Shop Main Street

Tinker Street (essentially Woodstock’s ‘Main St’), has so many amazing boutiques that you could spend a whole afternoon exploring. For example, Three Turtle Doves is a lovely vintage store that sells bohemian-style clothing and accessories that cater perfectly to the boho crowd. Of course, something you’ll want to add to your list of things to do in Woodstock NY!

Watch something at the Woodstock playhouse

And last on my list of things to do in Woodstock NY, it’s the playhouse! The local theatre, the Woodstock Playhouse is a great place to watch some local actors and art communities. You’ll find different groups putting on different shoes throughout the year, so it’s worth seeing whats on during your trip!

Where to stay in Woodstock, NY

If you’re visiting Woodstock NY (whether just for the night, or for a long weekend) you’ll want to find somewhere to stay in Woodstock. The good news is, Woodstock NY has loads of great accommodation options, and I’ve put my favourites into a list below for you to take a look at!

Here are my favourites places to stay in Woodstock NY….

Woodstock Way

First on my list of where to stay in Woodstock, it’s Woodstock Way which is a beautiful hotel which boasts both rustic cabins and modern suites. Catering to basically everyone with this combination, it’s got the bonus of being right next to a waterfall. This place has so many great spots, and all guests are permitted to use the common outdoor space that overlooks the falls. It’s consistently voted one of the best places to stay in Woodstock NY, so if you’re looking for something special, this is it.

places to stay in woodstock ny

Hotel Dylan

Located on Maverick Road, this hipster hotel, Hotel Dylan, is an 11-room boutique spot that celebrates the festival culture that’s prevalent in Woodstock. With rooms named after Jimmy Hendricks and other famous artists, you’ll find instruments lining the walls of this hotel.

A testament to the area’s culture, you can even take part in late night jam sessions should you wish to! Though this may not be the best pick if you like peace and quiet, it’s certainly a fun-loving and free-wheeling place to stay.

The Twin Gables

Next on my list of places to stay in Woodstock, it’s the Twin Gables. An excellent bed and breakfast located on Tinker Street, The Twin Gables has been operating since the 1920s. Decorated with art from local Woodstock artists, it’s a totally kitsch inn that should suit most budgets and tastes. The traditional exterior is so quirky and cool – we think you’ll love it.

The Woodstock Inn

This beautifully maintained and beautifully modern hotel in Woodstock is definitely a fantastic choice for where to stay in Woodstock NY. The rooms are cosy, but feel modern and luxurious too. This would make a perfect location for a weekend getaway or a romantic getaway.

ultimate guide to woodstock ny

Residence Inn Kingston

This is a big resort-style hotel, that is a little further out of Woodstock than some of the hotels on this list. However, if you want a big hotel with big hotel amenities then the Residence Inn Kingston, is a really great option for you. The rooms are well kept and modern and you’ll have lots of space too!

Where to eat in Woodstock, NY?

There are so many great places to eat in Woodstock NY! Here are some of my favourites…

Cucina Woodstock

First on my list of places to eat in Woodstock NY, it’s Cucina. Located in a beautifully restored farmhouse, this Italian restaurant radiates warmth and relaxation. With authentic yet contemporary Italian cuisine, it’s the perfect way to eat as the Italians do. With several large communal tables, it’s a fab place for a get-together or family meal. 

A top-tier favourite here are the grilled lamb chops with olive tapenade. With guests coming back here again and again, it’s a testament to just how good this joint’s food is! Make sure to make a reservation ahead of time if you can, because it can get busy. 

Bread Alone

Next on my list of places to stay in Woodstock, it’s Bread Alone. Located in the heart of Woodstock, Bread Alone is a family-owned bakery that’s been serving customers since 1983. Priding themselves on their use of organic grains and brick ovens, this place is THE place in Woodstock to come for baked goods.

Offering a casual menu of seasonal dishes as well, you can pick up light lunches of salads, soups and quiches in addition to a delicious loaf.

Mud Club

Serving up wood-fired bagels and delicious sandwiches, this place is a great quick-stop for a delicious bite to eat before setting out for the day. Selling some of New York state’s finest bagels, it should absolutely make its way onto your list!


And last on my list of places to stay in Woodstock, it’s Silvia! With its amazing interior design and equally amazing food, Silvia is a great option for those seeking a little bit of luxury. With a vine-wrapped pergola in its outdoor area, Silvia just screams sophistication.

Serving a great range of dishes, they pride themselves on back to basic cooking that’s sustainable. With a wood-fired grill and organic, vegetable-centric pantry, it’s the perfect place for a healthy bite. 

History of Woodstock, NY

I thought I’d end my ultimate guide to Woodstock NY, with a bit of history about the area!

In the gentle slopes of Overlook Mountain, you will find the beacon that sums up the individualism of the area. Not unlike many of New York’s other small towns, prior to the arrival of foreign settlers, Woodstock was home to numerous Native American tribes. Once the settlers made headway in the area, the land was cleared and by the 1800s, the economic focus of the town moved from farming to industry. 

By the 1930s, one of the main focuses of the area was tanning, which required a plentiful water supply and tannic acid that was obtained from Woodstock’s plentiful hemlock trees.

However, by the late 19th century, Woodstock preferred to focus on what could be found within the land than what could be gained from destroying it. Therefore, Woodstock turned itself to tourism, building hotels that were marketed as great places to escape the unhealthy air of New York City. Now, Woodstock is home to the arts, with festivals, concerts and plays being regularly shown here. 

Hopefully this guide to Woodstock NY has been helpful and inspiring for your trip!

It’s hopefully given you lots of ideas of where to stay in Woodstock, things to do in Woodstock NY and also all the amazing places to eat in Woodstock too! Woodstock is an amazing place with so much culture and personality – and you’ll love visiting!

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