The sounds of a drum circle beating its staccato rhythms confirmed my arrival in the heart of Woodstock, New York, the Catskill Mountains resort town forever linked to the iconic 1969 music festival. (The actual event took place 90 minutes away, due to a last-minute change.)
While Woodstock still trades on its hippie image, it offers much more than a nostalgia trip. Set amid the rolling landscape of the Hudson Valley, the area offers plenty to fill a long spring or summer weekend, from days spent shopping local boutiques, hiking protected trails, and checking out cultural and historic sites, to nights sipping craft cocktails, dining at locavore restaurants and taking in live performances.
Here’s a three-day itinerary that lets you mix and match activities—tie-dye strictly optional.
DAY ONE: LOCAL SHOPPING AND A MIDNIGHT RAMBLE
After arriving in Woodstock, get in the right mindset with a vegan lunch al fresco at Garden Café, and then meander along Tinker Street, one of the main drags. Here, you’ll find the Woodstock Artists Association & Museum, which holds regular exhibitions like the Upstate Art Weekend from July 18 to 21, and Woodstock Byrdcliffe Guild, whose events include the Annual Artists-in-Residence Show from May 4 to June 9 and the exhibition Pixerina Witcherina from June 22 to August 4. Indie stores and boutiques like the cozy book shop The Golden Notebook and Beck Home + Goods, spotlighting Hudson Valley makers, are worth a browse. Book a treatment at Woodstock Spa on three wooded acres for your own moment of zen.
With the day’s driving behind you, start your evening at the Early Terrible, a rustic, low-lit cocktail bar with an inviting deck. Continue with dinner at Silvia, which serves dishes made from organic, local and seasonal ingredients in an airy main dining room or on an expansive deck.
Afterward, at Levon Helm Studios, a venue founded by the late Rock & Roll Hall of Fame member and cofounder of The Band, you can attend a Midnight Ramble (on select nights) celebrating the rock songbook and other live shows. Local acts play regularly at The Colony, while the Woodstock Playhouse presents concerts as well as summer stock.
DAY TWO: HIKING AND HISTORY
Ready to fully embrace the mountain scenery? First, fuel up on a pecan sticky bun or an egg and cheese on brioche at Woodstock’s Bread Alone. Now, choose from an easy hike or a bike ride on the flat, tree-shaded 11.5-mile Ashokan Rail Trail just outside Woodstock for panoramic views of 3,140-foot-high Overlook Mountain. Or take the moderate 5-mile round-trip hike to Overlook’s peak for a bird’s-eye view of the Hudson River and beyond. If time allows—and the Phoenicia Flea market is being held nearby—plan a stop. The weekends-only market showcases locally made clothing, jewelry and artisanal products at more than a dozen roving sites.
Your next stop is Kingston, a small city along the Hudson that’s about 20 minutes from Woodstock. Dating to the mid-17th century, Kingston became the capital of New York in 1777 before British soldiers burned it down later that year. In the 1658 Stockade Historic District, you can see Four Corners, where all four buildings predate the Revolution, and take a walking tour led by the Friends of Historic Kingston. For lunch, stop by LOLA, a wood-fired pizza spot with a spacious patio. Afterward, peruse local shops along colonnade-covered walkways for clothing, kitchen and home items. Don’t miss the nearby Rough Draft Bar & Books, a bookshop and café known for its coffee and local beers.
Dinner is a show at Restaurant Kinsley, a New American restaurant with an open kitchen in a bustling, art-filled space that was the main banking floor in the building’s former life. Or pair dinner at Eliza, a Euro-inspired bistro in Midtown Kingston, with an actual show—anything from opera to comedy to jazz at the nearby Ulster Performing Arts Center.
DAY THREE: CHOOSE YOUR OWN ADVENTURE
Enjoy an early morning walk along the Hudson on Kingston’s Brickyard Trail, a nearly 2-mile stretch that provides broad views of the river. Stop for a bagel sandwich at Kingston Bread + Bar to mull the day’s options. Possibilities (all within a 90-minute drive) include Bethel Woods Center for the Arts on the site of the Woodstock festival and now the home of a museum, concerts and festivals; the contemporary art museum DIA Beacon; and several sites commemorating Franklin and Eleanor Roosevelt, including Hyde Park, their longtime home, and Val-Kill, Eleanor’s main residence after the death of her husband.
Finish your road trip with dinner at Butterfield, the main restaurant at Hasbrouck House, an 18th-century Dutch Colonial manor turned small luxury hotel. Set on 50 acres in nearby Stone Ridge, it’s the perfect spot to plan a return visit to this historic—and bucolic—retreat.
NOTABLE STAYS
IN-TOWN COMFORTS
Located in Kingston’s 1658 Stockade Historic District, Hotel Kinsley offers 42 rooms in a restored former bank and three nearby sites. Many rooms have gas fireplaces, and all feature luxe touches like marble-lined bathrooms and Frette linens. Continental breakfast is included.
TRIBUTE ACT
Each of the 22 guest rooms at Woodstock’s Hotel Dylan takes its name from one of the performers at the celebrated festival. The colorfully decorated rooms provide a turntable with a selection of vinyl, a mini Smeg fridge and LATHER bath products, while the property has a (seasonal) saltwater pool, firepits, a coffee shop and a Mexican restaurant.
