Woodstock, NY: A Complete Travel Guide (2024)

Disclaimer: this post may contain affiliate links, which at no cost to you I may earn a small commission.

Woodstock NY

Woodstock NY Complete Guide

Love, Peace, and Happiness. Welcome to Woodstock NY, a bohemian artsy town located in the Catskill Mountains just two hours away from NYC. This small town is a must-see when in New York State.

I spent a weekend in Woodstock and was completely transported to a unique town with adorable shops, great food, and a little adventure with the nearby hiking trails. Woodstock NY is definitely small, but you won’t feel overwhelmed with too much to do. You’re here to relax and I’ve got you covered on what to do while you’re here.

Here is a complete guide on Woodstock NY, from where to stay, top things to do, and where to eat for a fun year-round getaway.


What is Woodstock NY famous for?

You probably have heard of the Woodstock Festival before, the iconic music festival held in 1969. But it actually didn’t take place in Woodstock. The festival got its name from this town but held the actual event in Bethel NY, just an hour’s drive south of Woodstock NY.

Woodstock NY

How far is Woodstock NY from NY? 

Woodstock NY is the perfect weekend getaway from NYC because it’s only a 2 hour and 15-minute drive from the city. And while you can take a few routes, it’s a pretty straight drive on I-87 N.


Can you get to Woodstock without a car? 

It is possible to get to Woodstock without a car. You can either take a bus or train from NYC.

  • By Bus: 3 Hours, Price approx $35. Take the Port Authority Route to Woodstock (stop in Kingston, NY). Get off at the H. Houst & Son Hardware Store bus stop, which is located in the center of the downtown area in Woodstock. The West Hurley stop is about a 5-10 minute drive to the downtown area.
  • By Train: 2 Hours, Price approx $50+. Take the Amtrack train from New York Penn Station to Rhinecliff, NY. From there you’ll have to get a taxi or Uber for the rest of the 30-minute drive to Woodstock, NY.

However, to make the most of the surrounding area like hiking, or checking out other things to do, having a car will give you the most flexibility on your itinerary.

Be sure to bring these Travel Essentials for your trip.


Best Hotels in Woodstock, NY:

Hotel Dylan

Hotel Dylan (pictured above) is a newly renovated boutique hotel located on Route 28, about a 5-minute drive from Woodstock. Each room is named after a rock’n’roll legend and has a fun bold bohemian decor to go along with it, plus you have your very own record player.

Hotel Dylan expanded the original 11-room structure and added 11 rooms and a new lobby. The vibe is laid back with a heated pool that is opened seasonally, and cozy firepits on Friday and Saturday.

On-site there is Santa Fe, a Mexican restaurant, and Abandoned Hard Cider, which is a hard cider small shop and tasting room.

Prices Start: $130+/ night


Woodstock Way

Tucked behind a waterfall right off the main road in Woodstock is Woodstock Way, a contemporary hotel with a sustainable and conscious design. The property surrounding the tannery Brook River is made up of multiple cabins that serve as guest rooms, guest houses, and the Tannery.

The Tannery, which was on-site in the 1800s, is now the lobby and gathering space for guests to relax, have coffee, and shop.

Prices Start: $245+/ night


Twin Gables of Woodstock

Located right on the main road in Woodstock is Twin Gables of Woodstock, a family home built in 1880 that was established as a boutique hotel in 1926 by artists. This hotel was created for artists by artists and has uniquely designed rooms and common spaces.

You’ll have a feeling of home staying in this guest house.

Prices Start: $150+/ per night

RELATED: Weekend Getaways From NYC


Things to do in Woodstock, NY:

Mowers Flea Market

If you are heading to Woodstock on the weekend, a stop at the Mowers Flea Market is a must! You can find anything under the sun from books, clothing, home decor, you name it! It’s located at 11 Maple Lane, right off the main road in Woodstock.

You can pay $5.00 for parking, about a 5-minute walk away behind the Woodstock Pub. Or you can try to find free parking on the main road. Depending on your patience level, you might want to opt for a paid lot. It took me about 15 minutes to find a spot on the main road after circling a few times.


Open: Saturday & Sunday: 9 AM- 5 PM (May-October)

My Flea Market Find: I took home a vintage whiskey jug from the late 1800’s for $20. I thought it would be perfect for a vase in my apartment for tall flowers.

Woodstock NY

Woodstock NY

Walk throughout Mill Hill Road

Mill Hill Road is the main street in Woodstock that has plenty of shops, restaurants, and cafes. It won’t take you long to walk the entirety of the road. I recommend popping into all the shops as each one will offer unique finds!

Where to Shop in Woodstock, NY:


Glo Spa

Take the opportunity to relax at Glo Spa where you can take some time for yourself. Glo Spa is located right in the center of town and offers multiple kinds of treatments like facials, massages, peels, nails, and more. 

You can book a full-day package for multiple treatments, or add on a day pass for the steam, sauna, and locker room. 


Kaaterskill Falls

Kaaterskill Falls is a beautiful double waterfall located about a thirty-minute drive from Woodstock, NY.

There are a few trails where you can see the waterfall. The first is an easy hike to a viewing platform that looks down at the waterfall. The other is a hike down to the base of the fall.

Parking is on-site, however, due to the popularity of this activity, your car will be towed if parked illegally.

Tip: Wear appropriate shoes and only follow marked signs on the trail. Other paths may lead to erosion and chances of getting lost may heighten.


Overlook Mountain

Overlook Mountain

Ready for some adventure? Then a hike on Overlook Mountain is a must.

I’m shaking my head at thinking this was going to be a quick easy hike, but it was more of a steep uphill incline that took about 1 hour and 40 minutes one way alone. The scenery did not change much, but it was relaxing nonetheless. But it was a workout. (How people run and bike up this path is beyond me).

The trail itself is a rocky path so the right shoes are an absolute must, and you’ll have to watch where you step. Along the way, you will find the ruins of the Overlook Mountain Hotel which is a great opportunity for a small break to look around.

To get to the view you’ve climbed to see you have to reach the Overlook Fire tower. This is a tall metal structure offering the best views of the surrounding area. It’s worth a photo, but for how much we’ve climbed I was hoping for more views, so we followed a path near the Overlook Fire Tower and we found an incredible (somewhat hidden) view.

Parking: There is free parking to climb the Overlook Mountain at the Overlook Mountain entrance on Meads Mountain Road.

Timing: Plan for about 2 hours and 15 minutes minimum for the full climb up and down.

Caution: There are rattlesnakes in the area.


Woodstock, NY Restaurants

Bread Alone
Bread Alone

Bread Alone: Bread Alone is THE spot for your morning coffee decadent pastries, and sandwiches located in the center of town on Mill Hill Road. I visited every morning on my trip to Woodstock and I couldn’t recommend more!

Cucina: (Pictured Above) Cucina is a modern Italian restaurant located in a farmhouse with adorable front porch seating. This was one of my favorite dinner restaurants we visited. The cocktails were delicious, and the pizza and pasta were fantastic. This spot does get busy, so be sure to put in a reservation.

Silvia: Another popular new restaurant in Woodstock. Silvia is has a modern American menu that uses locally sourced ingredients and has a stunning dining and bar space.

The Woodstock Pub: A casual spot for lunch, The Woodstock Pub offers American and Mediterranean fare with plenty of beers on draft.

Photos courtesy of Phonecia Diner

Phonecia Diner: (Pictured Above)Built in 1962 and moved to the Catskills in the 80s, Phonecia Diner is an insta-worthy diner serving classic favorites with a modern twist. Food is sourced from the Catskills and Hudson Valley when available, and the drive from Woodstock is only 20 minutes.


Is Woodstock NY worth visiting? 

Yes, Woodstock NY is worth visiting!  While it’s a small town, it offers a cute charm with plenty of shops, and restaurants, a perfect destination for a relaxing getaway. Plus, compared to other towns in the area, Woodstock has more to see and do.

Related11 Best Weekend Getaways From NYC


Hope you enjoyed this Woodstock NY guide. Have you been to Woodstock? Let me know in the comments.

Save this post to your Pinterest boards:

Leave a Reply

Your email address will not be published. Required fields are marked *