13 Best Things to do in Woodstock NY

Now an eternal symbol of all things peace, love, and rock and roll (thanks to the Woodstock Music Festival of 1969), Woodstock is a small town in New York’s Catskill region that is home to some pretty rad activities.

So, if you’re looking for all the best things to do in Woodstock NY then this local’s guide is totally for you!

After all, I’ve lived in New York for 30+ years and want to share with you all of my secret tips for making the most out of your time in Woodstock.

This way, you can quickly and easily plan the Woodstock itinerary of your dreams as you channel your inner hippie and rock a sweet, sweet tie-dye t-shirt (far out, man).

Because in good old, Woodstock NY, you’ll find tons of interesting things to see, including vibrant art galleries, one-of-a-kind boutiques, delicious restaurants, exciting hiking trails, and vivacious outdoor markets – all of which are located about 100 miles north of New York City.

So, if you’re ready to start planning the Woodstock New York trip of your dreams, then grab some “special” brownies and swan dive into this post all about the all-time best things to do in Woodstock New York.

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How to Get to Woodstock NY from NYC

Good news for anyone looking to enjoy all of the best things to do in Woodstock NY. Because it is now easier than ever to travel from NYC to Woodstock NY.

So, all you really have to do is any of the following:

  • By Train – Hop on an Amtrak train that is headed towards Albany from Penn Station. Get off at Rhinecliff station and then take a taxi/uber from Rhinecliff to Woodstock. In total, the train ride should take about an hour and a half while the taxi/uber ride will take about 30 minutes.
  • By Bus (the easiest and cheapest way) – Hop on a bus from Port Authority Bus Terminal and take it directly to Woodstock. You may have to change buses in Kingston along the way but Trailways buses are great since they will basicallly plop you right in the center of town. In total, the trip will take around 2.5 hours, depending on traffic.
  • By Car – If you have a car and are traveling to Woodstock from somewhere other than NYC (who has a car in NYC?) then just hop on either 1-87 North or South and take this interstate to exit 19. Once there, just follow the signs to the center of town. It’s pretty easy and only takes around 2 hours to drive from NYC to Woodstock.

Best Hotels in Woodstock NY

The vibrant and fun common room of the Twin Gables of Woodstock bed and breakfast.
Image sourced from Hotels.com.

Guess what? There are a ton of great hotels for you to stay at during your trip to Woodstock NY.

However, to help make the entire trip planning process about 10,000 times easier, I’ve created this nifty little list of my picks for the best hotels in Woodstock NY.

So, whether you’re looking for budget, mid-range, or luxury accommodations, you’ll find something here to pique your interest. I pinkie promise (insert winkie emoji here).

  • Hotel Woodstock (budget, Woodstock) – With rooms that start at under $100 per night, this a great place to stay if you want a nice hotel room but are on a limited budget. Not only are these adult-only apartments well-located in the center of town (right across from the Trailways bus stop from NYC), but they sit inside an antique hotel that is now 148 years old. You’ll also love the loft-style apartments with 2 queen beds, a dining area, a living room and a kitchen. Although, you will have to ascend a spiral staircase to get to the bathroom on the 3rd floor.
  • Twin Gables of Woodstock (mid-range, Woodstock) – This cozy, well-reviewed bed and breakfast is located right in the center of town and features individually decorated rooms that include nifty things like 4-poster beds and antique furniture. And while there are no TVs in any of the rooms, guests have access to Wifi and a free Continental breakfast that is served daily (yum).
  • Morning Glory BnB (mid-range/high-end, Woodstock) – Easily one of my fave places to stay in Woodstock, this unique bed and breakfast sits inside a clapboard-style home and features lovely rooms that are outfitted with antique furniture and hardwood floors. Guests will also enjoy WiFi throughout and can use one of two rental kayaks. Continental breakfast is also served daily and live music can be enjoyed here in the evenings.
  • Hotel Dylan (Luxury, Woodstock) – This fun, Bohemian-style, 3-star hotel has vibrant, chic rooms that include WiFi, flat-screen TVs, coffee makers, and large sitting areas. There’s also a Mexican restaurant on-site and guests are welcome to use a seasonal outdoor pool and enjoy compimentery breakfast on the weekends.

Best Things to do in Woodstock NY

1. Visit Catskill Park and Hike Overlook Mountain

Sunset from the top of Overlook Mountain with fall foliage all around since this is one of the best things to do in Woodstock NY.

Hidden away in the heart of the Catskills region of New York, Woodstock is surrounded by more than 700,000 acres of wilderness.

Therefore, it’s really no surprise that one of the best things to do in Woodstock NY is, DUH, go for a hike. And one of the best places to do this is Catskill Park, aka the Catskill Forest Preserve.

After all, this natural wonderland was first established in ye olde 1885 and is home to some of the best hikes in upstate New York.

A fact that makes a whole hell of a lot more sense when you realize that this park has, count em’, 35 different peaks and ridges that exceed a height of 3,500 feet.

Yup, now that’s why I call serious elevation gain. So, feel free to hop on one of 19 different trails that will take you to the summit of some of these mighty mountains.

And along the way, keep an eye out for epic local wildlife that includes bobcats (rare but yikes), cougars (double yikes), fish, black bears, and various other adorable little creatures.

Also, while any of these trails are sure to inspire, you really can’t go wrong with an epic hike up Overlook Mountain to see the amazing ruins here.

After all, it’s the southernmost mountain in the entire range, stands at a whopping, 3,000+ feet tall, and offers intrepid hikers impressive panoramas that are next-level awesome.

2. Shop til’ You Drop on Tinker Street

The exterior of a colorful vintage shop in downtown New York.

Okay, before you even begin this shop fest of awesome, you MAY want to pick up (aka rent) a rad set of wheels from Overlook Bicycles.

Is renting a bike entirely necessary? No, especially since the downtown area of Woodstock is fairly small. But, going for a leisurely bike ride is deffo one of the best things to do in Woodstock NY on a warm, spring day.

Anyway, continue down Tinker Street and you’ll see a bunch of locally owned shops that get particularly awesome right when you hit Tannery Brook Road but before the entire road forks off into Rocky City Road and Mill Hill Road.

Some of my personal faves here include:

  • Headstock & Co – great boutique
  • Three Turtle Doves – vintage clothing store
  • The Center for Photography at Woodstock
  • Woodstock Byrdcliffe Guild – art gallery
  • Joshua’s Cafe – Try the butternut squash soup and lavender soda
  • Jean Turmo Ltd. – gift shop
  • Lily’s Boutique – hidden gems for any fashinistas out there
  • Rock City Vintage – vintage clothes
  • And so much more!

And although it’s technically not on Tinker Street, you should 100% stop at Bread Alone Bakery and get an almond croissant, a loaf of bread (they’re all good), a breakfast burrito, or a hot caramel latte.

Yeah, this bakery is exceptionally good even if the menu is small and their food isn’t the cheapest. But, per usual, you get what you pay for!

3. Check Out Ashokan Reservoir

View of Ashokan Reservoir in the Catskills at sunset, one of the best things to do in Woodstock NY.

Did you know that Ashokan Reservoir supplies NYC with most of its drinking water? Yup, crazy but totally true. And just another one of the pros of living in New York City since this water is some of the cleanest in the entire country.

Anyway, back to one of the best things to do in Woodstock NY because this gorgeous reservoir is just a short drive away from this tiny town in the Catskills.

And once you arrive, you’ll quickly see that this is one of the largest reservoirs in the US. So, stroll along the 2+ miles of trails here and take in the awe-inspiring views of the mountains that surround you. Also, be on the lookout for soaring bald eagles that occasionally make a guest appearance here.

Sadly though, you can’t swim in this reservoir. But, you can make use of the Ashokan Rail Trail – an 11.5-mile multi-use trail with signs that detail the history of the region and the development of the reservoir.

Pro Tip: The paved, 2.8-mile long Ashokan Reservoir Promenade is stunning and well worth your time.

4. Eat ALL the Food

Home made chicken parm and linguine from Cucina in Woodstock because this is one of the best things to do in Woodstock NY.

Contrary to what you might think, one of the best things to do in Woodstock NY is eat ALL the food. Because, trust me, the foodie scene really is that good.

But, it can be difficult to know where to start when you’re new to an area. Thankfully though, your friendly, New York local is here to show you the way and to make those pants of yours feel infinitely tighter by the end of this culinary tour de force.

So, some of my favie faves, which include:

  • Yum Yum Noodle Bar – They serve up delicious Japanese noodle bowls (super customizable) and Southeast Asian-style street food that made me (almost) feel like I was back in Asia,
  • Peace Love and Cupcakes – A family-owned bakery in Armory Square that sells really good chocolate chip cookies and great cookies and cream cupcakes. The staff are also REALLY friendly too.
  • Cucina – This sleek restaurant serves modern Italian cusiine inside an old farmhouse. Order a homemade lemon and thyme soda with a pear and goat cheese pizza and I promise you will NOT regret it.
  • Garden Café – As the name suggests, this adorable little eatery in the heart of Woodstock is a great vegan spot where you will hardcore DEVOUR the sweet pea guacomole. They also serve a great lasanga, a marco meal with tofu, delicious homemade hot sauce, and superb coffee. Honestly, it’s a great place to go even if you’re not vegan.

Also, just an FYI, this is not a full list of the best places to eat in Woodstock. These are just some of the places that I’ve dined at and that I thought were really good.

5. Check Out all the Local Art Galleries

Long before that iconic music festival took place in 1969, Woodstock was established in 1903 as a super rad, utopian artist’s community by the name of The Byrdcliffe colony.

In fact, The Byrdcliffe colony still exists today and was an all-around great place for artists to go and get all creative in the woods. So much so that a one, Bob Dylan was a former resident.

And with all this artistic greatness in the town’s history, it’s so small wonder that one of the best things to do in Woodstock NY is to visit the many art galleries that still exist here today.

So, if you want to channel your inner Vincent Van Gogh (minus cutting off your own ear), here are some great art galleries in the area.

  • James Cox Gallery – Showcases twentieth and twenty-first century American art
  • Elena Zang Gallery -Features contemporary fine art from ilocal and international artists living in the Mid-Hudson Valley. Works on display include paintings, prints, photography, sculpture and ceramics from more than twenty different artists.
  • Woodstock School of Art – They offer fun classes all year long in darwing, painting, printmaking, and sculpture. They also have an associated gallery that features work from students and teachers, as well as historically signifcant artists in the region.
  • Byrdcliffe Art Schools and Classes – This organization preserves historic art and offers a wide array of classes that anyone feeling a bit creative will love.

6. Stop by Karma Tryana Dharmachakra Monastery

Tibetan Temple with vibrant prayer flags out front.

Channel your inner hippie and head on over to Karma Tryana Dharmachakra.

It’s also fondly referred to as KTD for short and is an amazing Tibetan Buddhist Monastery that is home to one of the best things to do in Woodstock NY.

In fact, it’s the North American seat of His Holiness the 17th Gyalwang Karmapa and is a well-maintained complex, with stunning grounds that visitors will love to explore.

If you have time, stop by during the week and explore the grounds, which include eight stupas and an amazing main shrine room.

And if you happen to be in the area during the evening, then enjoy a Chenrezik sadhana and mantra chant from 7:00 pm -8:00 pm on weeknights, in the Tara Shrine Room.

Address: 335 Meads Mountain Rd, Woodstock, NY 12498

Hours: Open Monday through Friday from 10:00 am to 5:00 pm and then again from 7:00 pm to 8:00 pm.

Price: Free

7. Opus 40

View of the Opus 40 sculpture park with stunning green mountains in the background.

If you like art and getting back into the great outdoors, then Opus 40 is definitely one of the best things to do in Woodstock NY for you!

I mean, it’s a massive, 60-acre outdoor sculpture park and museum that sits right outside Woodstock in nearby Saugerties, New York.

So, stop by today and check out an enormous, handmade, environmental sculpture with stone ramps, platforms made of bluestone quarry, and pedestals that are truly awe-inspiring to behold – so much so that this Woodstock attraction is now a National Historic Registered site.

Because believe it or not, this one-of-a-kind piece is actually based on Aztec and Mayan stonework and took artist Harvey Fite more than forty years to complete (hence the name of this place).

Yeah, now that’s what I call dedication.

However, in addition to the sculpture itself, guests can also enjoy scenic nature walks, guided tours (about 30 minutes long, cost $25, and on weekends only), live music, theater, and so much more!

Pro Tip: Have lunch at the Papa’s Best Batch Food Truck that hangs out here on the weekend. I like the hummus but the brisket sliders are really good too since this food truck is known for its bbq.

Address: 356 George Sickle Rd, Saugerties, NY 12477

Hours: Open seasonally, from April through November, Thursday through Monday from 10:00 am to 5:00 pm.

Price: Standard tickets are $11, senior/student tickets are $9, and children 4 and under are free.

8. Explore Some Outdoor Markets

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Do you enjoy getting outside while simultaneously supporting small local businesses? If so then you’ll love the fact that Woodstock is home to a ton of different outdoor markets!

After all, you’ve got the much-loved Mower’s Flea Market on Saturdays and Sundays from 9:00 am to 5:00 pm.

It can be found just near the Village Green, on Maple Lane, and features a wide array of vendors that sell super snazzy things like jewelry, vintage clothes, fresh produce, old-school records, and fresh pizza.

Plus, there are usually live performances on-site that visitors will love to rock out to.

However, if you’re more of a foodie fanatic than a shopaholic, then you’ll love the Woodstock Farm Festival, which is a seasonal farmer’s market that is held from May through early October every year.

Open on Wednesdays from 3:00 pm to 6:45 pm (at the Mountainview parking lot), sellers here showcase the best eggs, baked goods, meats, cheeses, ice cream, and prepared foods in the region – making it an ideal place to shop and support local farmers and food producers.

9. Be Awed by the Woodstock Music Festival Site

Site marker for the Woodstock music festival.

I bet the first thing you think of when you hear, “Woodstock” is the iconic music festival, of the same name, that was held in the Catskills region in 1969.

Am I right? Hell yeah, I am since it’s easily the single most famous music festival in history. So, if you want to get in on some of the historic awesomeness then add the Woodstock Music Festival site to your list of the best things to do in Woodstock NY.

See, this glorious musical extravaganza was held from August 15th through August and 18th in 1969 and was advertised as, “3 Days of Peace and Music”.

Contrary to popular belief though, the Woodstock music festival was not actually held in Woodstock but 46 miles away in Bethel, on a dairy farm that belonged to Max Yasgur.

Therefore, if you want to step back in time and understand why this festival was so historically significant, be sure to visit the Woodstock Museum at the Bethel Woods Center for the Arts.

It features a wealth of multimedia displays and exhibits that explore the cultural and societal changes of the 1960s as they relate to the music festival.

Then, afterward, go just down the road to see the site marker for the actual music festival itself.

Address: 200 Hurd Rd, Bethel, NY 12720 (museum) and Hurd Rd, Swan Lake, NY 12783 (site marker)

Hours: Open daily from 10:00 am to 5:00 pm (museum) and the site marker is open twenty-four hours a day.

Price: Free (site marker) and tickets for adults (museum) are $17/$19.69, seniors (65+) are $15/$17, kids (6-18) are $8/$10, and children 5 and under are free.

10. Go Tubing or Fishing on Esopus Creek

Red bridge spanning Esopus Creek near Woodstock NY.

Not gonna lie, this definitely isn’t one of my favorite things to do in Woodstock NY. But, it’s a good activity to add to your Woodstock itinerary if you have a bit of extra time on your hands and want to be outside.

Especially since Esopus Creek is the largest and most well-known waterway in the area – providing visitors with ample recreational opportunities that include fishing for rainbow trout and tubing.

So, stop by Tinker Town Tubing (just outside Woodstock), grab some gear, and enjoy a leisurely, 26-mile float down this wonderful creek of awesome.

11. Experience Woodstock Waterfall Park

Waterfall in Woodstock Waterfall Park

Now, is Woodstock Waterfall Park home to one of the best waterfalls in New York? Umm, probably not.

However, it’s still a super scenic and incredibly relaxing place to go if you’re in search of some of the best things to do in Woodstock NY.

It’s also small. Like, 10 feet wide by 50 feet long small. But, what this park lacks in size it more than makes up for with awesome views.

So, stop by, check out the waterfall on Tannery Brook, and make the most of your time in Woodstock NY.

Address: 8 Tannery Brook Rd, Woodstock, NY 12498 (right near Tinker Street)

Hours: Open daily, twenty-four hours per day.

Price: Free

12. Catch a Show at the Woodstock Playhouse

Exterior of the Woodstock Playhouse in the eveing.
Image sourced from Woodstock Film Festival in Flickr.com.

Love live musical and theatrical performances? If so then stop by the Woodstock Playhouse sooner rather than later.

It’s an enchanting, historical theater that was first opened in 1938 and that is now home to beloved local events like the annual Woodstock Film Festival in the fall.

They also have an always fantastic, summer musical lineup that is not to be missed if you’re planning a summer visit to Woodstock, New York.

Address: 103 Mill Hill Rd, Woodstock, NY 12498

Hours: Showtimes vary by event but usually in the evening on the weekends.

Price: Varies by event but anywhere between $40 and $65 per person.

13. Enjoy Some Live Music

People enjoying a live concert.

Even though the Woodstock Music Festival 1969 is but a distant memory, there are still a ton of great places to enjoy live music in Woodstock NY.

So, if you’re looking to jam out as you check out all the best things to do in Woodstock NY, then try the Bearsville Theater for weekly indie concerts, the Maverick Series for summer concerts in the woods, and Levon Helm Studios.

In fact, the latter of these three music venues was started by the drummer from The Band, Levon Helm, and is known for hosting an uber-fab, Midnight Rambles show that features folk, indie, and rock music from all across the country.

And contrary to what the name might suggest, the Midnight Rambles show actually starts at 8:00 pm, not midnight.

But, if none of those options appeals to you, then you could hit up the Village Green since there’s always someone jamming out there during the summer. In particular, the Sunday drum circle is a pretty rad thing to see.

Map of the Best Things to do in Woodstock NY

Click here for the full map.

Additional New York Travel Resources You’ll Love

So, that just about concludes this guide to the best things to do in Woodstock NY.

Tell me, did your fave Woodstock attractions make the list? If not then let me know in the comments below so that I can check them out.

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