This Upstate New York Town Offers Mountain Views, Charming Hotels, & Farm-To-Table Dining

Many have grown up familiar with the very popular 1960s music festival that changed the way people gather and enjoy musical artists across the U.S. today. Although the festival was moved from its original location to a farm 60 miles southeast in Bethel, the name of the festival forever linked it to the small Catskills town of Woodstock, New York. This vibrant, artistic town continues to encapsulate the same laid-back, free-spirited energy of the '60s, but in a more picturesque way than perhaps the famous imagery of hippies covered in mud. Today, this quaint town attracts travelers with its inspiring mixture of mountain tranquility, bohemian energy, and small town charm. 

Just a two-hour drive from New York City, Woodstock is the perfect weekend escape from the hustle and bustle of city life. Visitors can spend their days exploring nearby nature trails that wind through the scenic Catskill Mountains, enjoying the ever-changing collection of shops and galleries along Woodstock's main drag, and grabbing a bite at one of the town's popular eateries.

Whether it's spending your time browsing the weekend flea market, perusing the shelves of a local bookstore, sipping a warm coffee at a cozy cafe, or attending a live music event, Woodstock is the perfect place to unwind and enjoy a peaceful retreat. With its welcoming community, mountain charm, and artistic vibes, Woodstock remains one of upstate New York's most beloved small town getaways — a place where relaxation and inspiration come together as naturally as flower crowns on hippies.

A visit to Woodstock wouldn't be considered complete without exploring the main thoroughfare, Tinker Street. Once a street lined with shops carrying tie-dye t-shirts and products for the loveable stoner in your life, now visitors will find stores with everything from vintage clothing, locally-made home goods, books, a funky candle shop, and art. Before heading out to explore the natural beauty surrounding Woodstock, fuel up at Tinker Taco Lab with scrumptious handmade tacos and tamales. 

Then, go enjoy some of Woodstock's natural settings, like the Overlook Mountain Trail, offering a moderate hike past the haunting stone ruins of the old Overlook Mountain House before reaching gorgeous, panoramic views of the Hudson Valley from the summit fire tower. For an even more tranquil experience, visit the Karma Triyana Dharmachakra Monastery, a serene Tibetan Buddhist retreat perched above town, where visitors are welcome to explore the grounds, take a guided tour on weekends, and join a meditation session. After a day spent exploring, choose from one of the town's charming farm-to-table dining experiences, like Restaurant Silvia, which serves up delicious, fresh ingredients cooked in an open-kitchen setting, or Cucina, serving up classic Italian fare in a restored farmhouse. 

As evening settles in over this spirited town, Woodstock comes alive once more, this time through its community's love for music. The iconic institution, Levon Helm's Studio, has been at the heart of that tradition for decades. Founded by the late drummer of The Band, the studio continues to host shows, including the legendary Helm Family Midnight Rambles, playing iconic music from The Band and Helm himself. Longstanding Bearsville Theater, a short drive away, continues to honor the town's legendary musical heritage as well, with live performances ranging from folk and jazz to indie and blues. 

Thankfully, Woodstock's ever-changing development means visitors don't have to sleep in makeshift tents out in muddy fields like back in the '60s. No, surprisingly for a small town, Woodstock is filled with charming accommodations to spend a night or weekend enjoying the area. Those seeking a spot within walking distance of Tinker Street should consider Twin Gables of Woodstock, a uniquely funky boutique hotel with individually-styled artsy rooms. The Herwood Inn is another more rustic spot close to downtown, with barn-style apartments, a hot tub, and contemporary decor. For travelers wanting to fully embrace nature, a stay at Woodstock Way Hotel is an excellent choice, with beautiful mountain and forest views and rustic designs. Hotel Dylan — just a few minutes outside of town — is a great spot for music lovers, as its rooms deliver playful, music-inspired décor and a relaxed, retro vibe. 

There are a few different options for getting to Woodstock from New York City. To drive, it'll take about two hours, and it's basically a straight shot down I-87 North. It's possible to get here by public transport, but as always with public transport in the U.S., it's a bit trickier. The bus, operated by Mega Bus, takes about 2.5 hours. It leaves from the Port Authority Bus Terminal in New York City, and drops travelers at Pine Hill Trailways Bus Stop in Woodstock, about a 20-minute walk from town.

Visitors wishing to take the train can hop aboard the Amtrak from New York Penn Station to Rhinecliff, where you'll need to catch a 30-minute taxi or Uber into town. No matter how you decide to arrive, Woodstock will be waiting to welcome you with open arms, fresh mountain air, and the unmistakable creative energy that has defined this town for decades.