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How To Plan The Perfect Weekend Getaway From NYC To Woodstock

Updated: Jul 31

If you are looking for a short getaway from NYC, head to Woodstock, NY, a bohemian paradise nestled in the Catskill Mountains about two hours from Manhattan. Visiting Woodstock for a weekend trip from NYC will give you an ideal getaway experience. You will feel like you have been entirely transported to a unique town with charming shops, wonderful food, and a little adventure. Woodstock, New York, is a small town, yet there isn't a shortage of things to do.


If you're waiting for the best weekend getaway from New York City, look no further than this detailed Woodstock NY travel guide - Find out how to get there and what to see and do.

Where To Stay In Woodstock, NY?

Book a room at the historical Twin Gables Guest House in the heart of Woodstock, one of the best boutique hotels in the area to stay during your weekend getaway from NYC. Artists Alfred and Mabel Daiber (of Brooklyn, NY) bought the 19th-century mansion at the height of Woodstock's fame as a hub for artists and turned it into a Boutique Hotel in 1926. Twin Gables has become a staple in the area ever since. This charming boutique hotel with an impressive ambience and a homey feel was recently purchased by creative family-run company Verdigreen Hotels & Residences, whose mission is to breeze new life into the properties while highlighting their character and uniqueness.

Guest rooms at Twin Gables are bright and airy, with hand-selected artwork throughout. Every room has a theme with unique pieces of furniture and decor, inspired by one of the numerous stories that took place at the guest house. Make sure to ask the innkeeper ! The property also has suites with living areas and private baths. In The Parlor, you can unwind with a cup of tea from the coffee nook and a book from our well-curated library. The rainbow stairwell leads up to the second and third storey of The Twin Gables, where you'll find the serene Meditation Room in the attic. Meditate, practice yoga, or relax with a professional massage (by appointment only). Breakfast is served daily in the kitchen. Once you have unpacked and rested, make your way to Woodstock's various attractions.


A Weekend In Woodstock: Attractions And Things To Do

Mowers Flea Market:

The Mowers Flea Market is a must-visit if you're in Woodstock this weekend. Everything from books to clothing to home decor and more may be found here! The address is 11 Maple Lane, just off Woodstock's main thoroughfare. Parking is available behind the Woodstock Pub for a fee of $5 per vehicle, and it takes about 5 minutes to get there on foot. Alternatively, you can look for free parking along the highway.

Go For A Walk Along Mill Hill Road:

Shops, restaurants, and cafes flourish on Woodstock's main street, Mill Hill Road. Walking the entire length of the road won't take you long. A visit to each store is highly recommended, as they all have something unique to offer.

However, we'd like to recommend a couple of our favorite stores:

Mirabai Bookstore: Unique store for books, gifts, and more

Everyday Magic: Goods with a Purpose + Healing

Candlestick: A store stocked with candles and other little trinkets

Woodstock Bring Your Own: A replenishment and sustainable living store that sells home items, books, personal care, and more.


The Falls Of Kaaterskill:

It takes around 30 minutes to get to the stunning Kaaterskill Falls from Woodstock, NY, thanks to a scenic drive through the Adirondack Mountains.


Overlook Mountain:

If you want adventure, hike the many Overlook Mountain trails. Along the way, you will see the ruins of the Overlook Mountain Hotel. When you reach the Overlook Fire tower, stop and look around you. Definitely worthy of a photograph.


Woodstock Artists Cemetery:

Before hitting the road, take a peaceful tour through the Woodstock Artists Cemetery to honour individuals who have contributed to the region's illustrious artistic tradition. The restored area includes finely sculpted bluestone burial markers to serve as memories of Woodstock’s various offerings to the creative world over time.

Where to Eat and Drink in Woodstock?

With a wide variety of restaurants and bars, Woodstock is a wonderful spot to eat and drink your way through the best weekend getaway from NYC.

  • When it comes to breakfast, Mud Club does it right with their wood-fired bagels and delectable spreads. Other options include a selection of pastries and sandwiches.

  • Bread Alone has multiple locations, a local favorite as a quick-and-easy bakery.

  • Garden Cafe Woodstock is an excellent choice for a casual lunch or dinner. Fresh, local & vegan seasonal food in a charming location that overlooks the town's primary park.

  • Tinker Taco Lab, which offers al fresco inside dining with its intimate bar, is another great place worth mentioning.

  • YumYum Noodle Bar is a casual sit-down asion fusion type of establishment, perfect for those who can’t pass on a bowl of delicious noodles.

  • At Silvia, the magnificent interior design and delectable cuisine are fantastic for a more formal sit-down supper.

  • Another long-standing Woodstock icon is Cucina, which serves modern Italian cuisine in a beautifully renovated 18th-century farmhouse.


The town of Woodstock is home to several fantastic establishments to enjoy a glass of beer, wine or curated cocktail. The recently opened Tinker Street Tavern is one of our favorites. It was built by the famous Brooklyn restaurateurs of Skinny Dennis & Do or Dive and has a unique indoor/outdoor setting, lively cocktail and food menu and live music. Early Terrible has a date night romantic atmosphere and a range of natural wines and finger foods that will swoon you. Cheers! For those who enjoy craft beer, Woodstock Brewing's taproom is located just outside of town, and it's a fantastic place to relax with a pint and a snack. It's a nice place to kick back and have a few beers on weekend nights.


Is It Worth Planning A Short Getaway From Nyc To Woodstock?

A trip to Woodstock, New York, is well worth it! Woodstock has a charming atmosphere and plenty of stores, restaurants and boutique hotels, making it an ideal destination for a peaceful weekend getaway from NYC. It is an ideal short getaway from NYC offering some of the best outdoor adventures, nightlife, foods, and sightseeing to enjoy. Make sure to book your room at Twin Gables Guest House - one of Woodstock's best hotels to topple your best weekend getaway from NY yet!



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