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Fall Weekend in Woodstock, NY

Fall Weekend in Woodstock, NY

My family and I wanted to take a road trip together for the weekend to see some fall foliage. We thought Catskills was the perfect weekend getaway since it is only a two hour drive. We decided to stay in the bohemian artsy town of Woodstock, New York. Here is a complete guide of where to stay, things to do, and where to eat to spend a fall weekend in Woodstock, NY.

Fall Weekend in Woodstock

Where to Stay

Fall Weekend in Woodstock


Hotel Dylan

This is a fun boutique hotel that is a 10 min drive to the center of town. On site, they have a Mexican restaurant called Santa Fe and a cider tasting room called Abandoned Hard Cider. They also have a swimming pool and an outdoor fire pit.

Woodstock Way

This is a contemporary hotel with a sustainable and conscious design. It’s walking distance to the town center.

Twin Gables of Woodstock

This is a cute bed and breakfast that is located right in the center of downtown.


An Airbnb is also a great option! My family and I found the cutest Airbnb that was a 10 minute drive into town. It is a beautiful renovated old barn with a chic, modern, and eclectic design. This home was equipped with everything we needed – full stocked kitchen, bathroom supplies, games, indoor fireplace, and an outdoor fire pit! It has all the modern amenities and aesthetics, while retaining all the charm and character of a period structure.

Things to Do

Explore Woodstock Town Center

Mill Hill Road is the main street of Woodstock and it’s where you will find all the cool shops, restaurants, and cafes.

Katerskill Falls

This is a beautiful two stage waterfall located in the eastern Catskill mountains. It is only a thirty minute drive from Woodstock. It is an easy 1.4 mile round trip. The trail starts at a viewing platform where you can look down to the waterfall. This also makes a great photo spot to see fall foliage views. The next part of the trail takes you to the base of the falls.

This is a very popular hike so I highly recommend you get there early. We got there at 10am and we waited two hours in line to get a parking spot!

Overlook Mountain

This hike ends at the top of a fire tower, where you will get an amazing view of the Catskills and even the Hudson Valley! This is a difficult 5 mile hike so be prepared for a steep uphill climb! We didn’t have time to go on this hike, but I want to do this the next time we visit the Catskills!

Catskills Rail Explorers

Take a tour with Rail Explorers through the fall foliage! This is a pedal powered vehicle that rides on railroad tracks. It is an eight mile roundtrip that takes about 2.5 hours. This is a popular activity so I highly recommend you book at least a month in advance, or earlier if you are going during peak fall foliage.

Places to Eat

Phoenicia Diner

This is a modern Italian restaurant located in a farmhouse. Their food is amazing! We went there for dinner on our first night. My favorite was their shrimp linguine with jalapeños and tomato sauce. They get pretty busy so I recommend making a reservation.

Phoenicia Diner

This is a popular diner famous for its all day breakfast. They are on a first come, first serve basis so no reservations are required. We got there around 9 am on Saturday morning and there was no wait!


This is a cute spot that serves breakfast, lunch, and dinner. We went for lunch and it was so good! We loved their burgers and grilled cheese. I also tried their grain salad which was so yummy!

The Woodstock Pub

This is a great casual spot for lunch that offers American and Mediterranean dishes with a bunch of beers on tap.

Bread Alone

This spot is a MUST if you are in Woodstock. We stopped there for breakfast on the way home and it was so good! It is a great breakfast spot for coffee, pastries, and sandwiches.

Hope you enjoyed my guide on how to spend a fall weekend in Woodstock, New York!

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