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4 Unique Places to Visit This Summer in Woodstock, NY

Updated: Oct 10

Welcome to the town of Woodstock, New York—home to many interesting destinations that are worth checking out this summer. Whether you're looking for an upstate New York vacation or just a weekend break, Woodstock has something for everyone!


Woodstock is more than just a charming town at the foot of the Catskill Mountains. It is also a lively cultural center. A trip to Upstate NY is not complete until you explore the town of Woodstock. Indoor and outdoor activities, local boutique and antique shopping, delicious farm-to-table dining opportunities, and fun bar scene juts to name a few. Within an hour's drive of New York City, visitors find themselves in a different world, one that values small businesses and products made right here in the United States.


If you're keen to know more about what makes Woodstock, New York, so special, take a look at our list of the best unique places and hidden gems to explore!


The Best Places to Explore in Woodstock


Overlook Mountain

Overlook Mountain in Woodstock, New York is an excellent place to go hiking if you're seeking to get some fresh air. The trailhead parking areas are immediate across the street from the monastery, so you can check out two of Woodstock's top attractions in one day!

One of the Catskill Mountains' five remaining fire towers can be found atop Overlook Mountain, which dominates the Overlook Mountain Wild Forest area of Catskill Park. Visitors can take a 9-mile hiking trek from Fire Town to Echo Lake that includes the Ledges and winds around the mountain.


Karma Triyana Dharmachakra Tibetan Buddhist Monastery:

The Karma Triyana Dharmachakra (KTD) is a Buddhist monastery, built on the mountain overlooking Woodstock. Be sure to pay a visit to the monastery on your way back down the mountain. The white, crimson, and gold architecture appears to be tucked into the Himalayas' foothills. Flapping prayer flags and a massive golden Buddha grace the interior, further highlighting the metamorphosis. There is a bookstore at the KTD monastery, as well as weekend guided excursions. Public classes and meditation retreats are also offered regularly.


Holy Transfiguration Church:

You may find the rustic Holy Transfiguration Church near Woodstock, New York while moving towards the Overlook mountain trail. You can easily spot it adjacent to the Buddhist monastery. This church is a great option for those searching for something off the main road. An incredibly historic church in Woodstock. There is a baptismal pool in a separate building to the left. The church's doors are always open, and you are welcome to pray for as long as you like!

Ashokan Reservoir:

After exploring Woodstock, pay a visit to the Ashokan Reservoir in Catskill Park to get a cool breeze. When it comes to New York City's water supply, this reservoir is just one of many in the area. This reservoir is also the city's deepest, at a depth of 190 feet. Beautiful views of the Catskill Mountains could be seen from the paved waterfront trail that runs along the reservoir.

Pick Twin Gables As One Of Your Favorite Places To Stay in Woodstock, NY

Exploring the town of Woodstock and nearby areas can take days, which is why we recommend spending at least a weekend, if not a few extra nights, to enjoy all unique Woodstock attractions. There are plenty of places to stay near Woodstock, NY, but if you want to truly experience the heart and soul of the town, stay at our historical Woodstock bed and breakfast Twin Gables Guest House. Book one of our carefully designed, airy guest rooms or spacious suites with private baths. Twin Gables is a little art hotel with an extravagant, magnificent aura and true comfort of home.

Book your visit now!



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