About 100 miles north of the city — or a two-hour drive without traffic — Woodstock and the surrounding small towns in the Catskill Mountains brim with clean air, arty finds and outdoor adventure.
In the 50 years since the legendary summer of 1969, Woodstock has evolved from a tie-dyed hippie holdout into a stylish enclave for good living with crunchy local restaurants, thoughtfully stocked small shops as cool as anything you’ll find in Williamsburg, and a wave of new and refreshed boutique hotels.
If your vision of the Catskills begins and ends with "Dirty Dancing," you’ll still find that kitschy summer-camp vibe — from fly-fishing to roasting smores around the firepit — but you’ll also discover creative New Yorkers running their dream restaurants, hotels and breweries without ruining the original spirit of the place.
With the OG of summer music festivals marking its 50th anniversary this summer — and the tribute, three-day Woodstock 50 festival slated for August 16-18 in an undisclosed new location — get your tie-dye fix at the throwback-y Woodstock Legends shop (71 Tinker St.) cluttered with T-shirts, cannabis paraphernalia and life-size Blues Brothers statues out front. Also check out the lower-key, but still hippie-inspired Happylife Productions store (54C Tinker St., 845-679-6689, happylifeproductions.com) across the street. With nostalgia covered, get up to speed on modern Woodstock and browse the impeccably styled Three Turtle Doves vintage store (62B Tinker St., IG @threeturtledoves) and the gallery-like D-Day boutique (60 Tinker St., ddaystudio.com).
For lunch, head to Oriole 9 (17 Tinker St., 845-679-5763, oriole9.com), a cute cafe serving bistro fare, from goat-cheese omelets to curried coconut tofu hash, and cocktails, or the rustic chic Garden Cafe (6 Old Forge Rd., 845-679-3600, thegardencafewoodstock.com) for 100 percent plant-based, vegan food, including a tasty kids’ menu.
Next, take a ride over to 4.6-mile Overlook Mountain Trail for a moderate hike, passing by the ruins of a 19th-century luxury hotel and a fire tower at the top, or head to the sculpture park Opus 40 (50 Fite Rd., opus40.org) carved into a onetime bluestone quarry in Saugerties.
In the evening, savor Asian-inspired farm-to-table dishes from chef Doris Choi at Silvia (42 Mill Hill Rd., 845-679-4242, silviawoodstockny.com), which has art-lined walls and indoor and outdoor seating.
Have a quick breakfast at Bread Alone Bakery (22 Mill Hill Rd., 845- 679-2108, breadalone.com), a homegrown local baking company specializing in organic breads. Then learn how to fly-fish with Esopus Creel (5579 NY-28, Phoenicia, 845-303-9466, esopuscreel.com), which offers customized lessons and expeditions for all levels, or spend the afternoon exploring the lovely Kenneth L. Wilson State Park, which has dog-friendly grounds.
Recharge with lunch at Shindig (1 Tinker St., 845-684-7091, woodstockshindig.com), a hip restaurant at the beginning of Tinker Street, showcasing local purveyors, healthy comfort food — including a yummy grilled cheese plate with a mini serving of tomato soup — and quirky merch like a to-go mason jar. They’ve also got the best coffee in town and freshly baked pies.
Schedule a massage or a facial at Glo Spa Woodstock (62 Ricks Rd., 845-679-7800, glospawoodstock.com) — or a blowout at the adjoining Le Shag salon — and decompress in the beautifully designed relaxation room or cutting-edge O2 chair. It’s an oasis of calm run by three local women offering unisex services — and there’s a drop-in fitness club on the lower level.
Afterward, enjoy a scenic ride to Peekamoose Restaurant (8373 State Rte. 28, Big Indian, 845-254–6500, peekamooserestaurant.com) for dinner in the folk-art-inspired dining room or a cocktail in the cool back bar. Order a few apps to share, like the caramelized scallops and mushroom risotto, before your mains and save room for the house-made ice cream.
Back in Woodstock, check out a band (or stick around until Monday for open mic) at Colony (22 Rock City Rd., 845-679-7625, colonywoodstock.com), a 1929 venue reopened in 2017.
Good to know
Getting there: You can take the bus to Woodstock, which takes around 2 to 3 hours, but driving is most convenient since having a car is essential in the Catskills.
Getting around: For a weekend, there is plenty to do around Woodstock by foot or bike, however, having a set of motorized wheels will facilitate getting places.
Where to stay: Hidden behind Tinker Street steps from the center of town, the 12-room Woodstock Way (10 Waterfall Way, 845-684-5911, woodstockway.com), which opened in September 2018, overlooks a small waterfall and brook. The sustainably designed property features live green roofs, reclaimed wood and loads of local pride starting with a large portrait of the late local musician Levon Helm made entirely of bottlecaps in the reception area, which also doubles as a café. Each room is distinctively designed and comes with a record player and curated record collection. In nearby Phoenicia, the 20-room Graham & Co. (80 Route 214, Phoenicia, 845-688-7871, thegrahamandco.com) debuted a brand-new, two-bedroom bungalow this season and has a fleet of complimentary bikes for borrow. The hotel has a full range of rooms, from deluxe doubles with kitchenettes to bunk rooms with shared bathrooms.