Just over two hours from Manhattan, The Leeway is a picturesque, nine-room boutique motel in Mt. Tremper, NY. Previously Kate’s Lazy Meadow, the iconic hotel kept many of the charming details that made Kate’s so special, while a much-needed facelift brought its three buildings up to modern speed. The result is a one-of-a-kind Catskills experience, blending nature & camp vibes with sophisticated mid-century & modern design.

The crown gem is the riverfront area, accessed through a narrow tunnel of flora and fauna — where guests enjoy private Esopus Creek frontage with breathtaking mountain views. This magical area ringed by tall mountains and towering pine trees serves as Leeway’s social hub, with picnic tables, grills, Adirondack chairs, and a bonfire area with benches for guests. A large, sunny opening by the river is the ideal spot to spend days dipping in the river, bird watching, sun bathing, reading, playing fetch with the dog, or fly fishing.

While you’re in town, make use of your proximity to Kingston, Phoenicia, and Woodstock. Musically inclined guests should check out calendars at Levon Helm Barn (legendary!), Bearsville Theater, and Kingston’s Tubby’s – all of which get great shows. Other nearby cultural attractions include outdoor sculpture park Opus 40 or Woodstock’s Center for Photography.

Views from the Ashokan Quarry Trail in Olivebridge, NY. Photo by Escape Brooklyn.

For those seeking outdoor adventure, there’s no shortage of hikes and outdoor recreation in the area. One of our all-time favorite hikes is the nearby Overlook Mountain in Woodstock. About ten minutes from Main Street Woodstock, this 4.5 mile loop takes about three hours round-trip, with some time added in at the top for sight-seeing at the top. Features include a fire tower with 360º views (one of six in the region), and ruins from a grand mountaintop hotel that burned down (several times) to explore. Heads up: this popular trail is pretty well known; adjust your expectations and schedule accordingly, getting there early for parking and avoiding the crowds. Also, come prepared: it’s no short stroll in the woods! Come prepared with proper footwear, and bring plenty of water.

A lesser known trail with similar views is Mt. Tremper Fire Tower, whose six-mile trek also offers stunning 360º views from its own fire tower. Also nearby is the Ashokan Quarry Trail, a short 2 mile trail with incredible mountain overlooks. For a flat-surface trail with views – great for walking, running or biking – head to the Ashokan Reservoir Promenade. This no-car paved road is beautiful at any time of day, but especially at sunset.

Last, guests can and should try their hand at fly-fishing. Most people don’t realize (especially non-fishermen and women) that the Catskills was the birthplace of American dry fly fishing – and is known around the world for it. This spring and fall sport gets you out on the relaxing water, where even if you don’t catch anything, it’s a lovely way to spend a day. More experienced guests can use The Leeway as a home base to walk up and down the Esopus Creek for fishing. First-timers would be best hiring a guide to show you the ropes; inquire with The Leeway to arrange.

Beloved Silvia restaurant in Woodstock, NY, about 15 minutes from The Leeway. Photo: Escape Brooklyn

For breakfast or lunch, check out the famous Phoenicia Diner for a modern take on classic comfort food at this old-school, locally focused diner. To beat the crowds, go on the early side. Alternately, Bread Alone is amazing and you can stock up on pre-made foods to bring back to the hotel.

The best restaurant in close proximity is The Pines, whose cozy restaurant in nearby Mt. Tremper serves up elevated but non-pretentious fare like burgers, grain bowls and sausage plates. In summer, the back yard has its own hot dog menu (with walk-up service) called The Dog House, which paired with live music and performances, is the best vibe around. At this popular outdoor spot, picnic tables fill up quickly; bring a blanket for easy seating.

During off-season, or off-days (Sunday and Monday nights) check out nearby Foxfire Mountain House; this in-demand venue is booked most weekends for for weddings, but when it’s not, it’s three-course tasting menu in the dreamiest Bohemian inn, is a recipe for memories.

About 15 minutes away, the town of Woodstock has loads of good options including date-night appropriate Good Night and its sister restaurant Silvia. Before either, grab a drink at new cocktail bar Small Talk. For more casual vibes, check out Tinker Street Tavern for fun drinks and live music, Woodstock Brewing for local craft brews and snacks, or classic dive bar Boiceville Inn with a pool table, and cheap beer.

Reservations are recommended for upscale restaurants, especially during peak seasons. Always check current operating hours as they may vary seasonally!

Last, to stock up on provisions, stop at Adams Fairacre Farms on the trip up; this enormous grocery store is a downstaters dream, with loads of farm fresh food but also a huge garden center. Closer to The Leeway, a stop at Local Goods is recommended to stock up on drinks, dry goods and perhaps a little Catskills keepsake. If you think you’ll miss their open hours, they’ll curate a little pick-up basket for you! Just reach out.