Eat & drink
The best part of a group weekend: nobody has to cook — unless they want to.
Sorted by how far you'll have to drive. The starred spots are our personal favorites — the ones we press into everybody's hands the first time they visit.
Right down the road
Julia's Local
≈ 5 minRustic-elegant American cooking with a Scandinavian streak — trout done half a dozen ways, natural wine, and a dining room hung with the owner's own art.
Why we love it: Basically our neighbor, and the whole mood — bright, warm, a little Nordic — is exactly what we were going for at the house. Book ahead; the room's small and the locals know.
See and Be Kitchen
≈ 10 minA husband-and-wife bakery milling their own flour for the breads and croissants, plus genuinely great sandwiches to take with you.
Why we love it: Grab a stack of sandwiches for the trail — and do not, under any circumstances, leave without the chocolate babka. It's the best thing we've found up here, full stop. We love the coffee here, too.
Red Star Cafe & Bakery
≈ 10 minA cozy country café on Cairo's Main Street — proper coffee, a case full of pastries, and sandwiches and salads to go.
Why we love it: Your first-coffee-of-the-morning spot, and the right place to load up before you point the car at Windham.
Log Cabin Cafe & General Store
≈ 7 minNo-frills, homemade breakfast and lunch in Purling, with a little general store attached for coffee and snacks.
Good to know: Exactly what a slow morning wants — big omelets, hearty plates, easy prices, five minutes away.
Mateo's Pizza
≈ 10 min · deliversFamily-run, New York-style pizzeria in the middle of Cairo — classic pies, garlic knots, wings, the works.
Why we love it: The hero of the low-key night in. They deliver straight to the house, so it's the move after a long hike or a late check-in. Insider tip: ask for the off-menu "Round Top" pizza — you have to call for it, and it's worth the phone call.
Worth the short drive
Hemlock
≈ 20 minA tiny, low-lit cocktail bar in the village of Catskill — routinely named one of the best bars in the country — with a short but serious kitchen.
Why we love it: Come for the cocktails, stay for the smash burger, which gets our vote for best burger around. Evenings only, and more date-night than family-night.
Gracie's Luncheonette
≈ 15 minScratch-made diner food in Leeds — house breads, cured bacon, loaded plates, and a case of donuts and pies baked that morning.
Good to know: Our pick for a proper sit-down breakfast. Get a box of donuts for the road, then put them in the trunk so they actually make it home.
Cone-E Island Ice Cream
≈ 20 minSoft-serve frozen custard and thirty-some homemade hard flavors at picnic tables right on the Catskill Creek. Gluten-free cones, too.
Why we love it: The perfect end to a hot afternoon and an easy crowd-pleaser. Seasonal — spring through summer.
For a big night out
The Maker
≈ 40 minInside a jewel-box boutique hotel on Hudson's Warren Street: a speakeasy lounge in an old carriage house, plus a glass-conservatory restaurant and café.
Why we love it: Our favorite Hudson evening — start with a cocktail in the lounge (ask about the fragrance cocktails), then dinner or a slow wander down Warren Street. Works for just-drinks or the whole night.
Matilda
≈ 30 minSerious farm-to-table cooking inside The Henson hotel in Hensonville, from the team behind Michelin-starred Contra and Wildair.
Why we love it: The fanciest dinner up here, in a cozy cabin room with a real fire. Save it for the birthday or the big toast — and book well ahead.
= a house favorite. Drive times are rough, from the front door.
Get outside
Yes, the hot tub counts as an activity. But trust us on the ridge.
Three walks we love, from a flat stroll anyone can do in sneakers to a proper ridge climb. Bring water, check the forecast, and put the good shoes on for the longer two.
The Windham Path
Easy · ≈ 30 min driveA flat, gravel 1.5-mile loop through meadows along the Batavia Kill, with a covered bridge and wide-open mountain views. Wildflowers in summer, pure gold in October.
Good to know: The easiest beautiful walk around — stroller- and wheelchair-friendly, and lovely for every age and energy level. About 45 minutes at an amble; a connector adds a mile if you want more. Park on Route 23 just outside Windham village.
The Ashokan Rail Trail
Easy · ≈ 50 min driveA flat, crushed-stone rail trail running 11.5 miles along the north shore of the Ashokan Reservoir, with wide-open water-and-mountain views most of the way. Walk a mile, or bike the whole thing.
Good to know: The best bring-everyone option — stroller- and wheelchair-friendly, leashed dogs welcome, and an absolute stunner in fall. It's the longest drive on this list, but the reservoir framed by the High Peaks earns it. Bring bikes if you've got them, start at the Woodstock Dike trailhead (east end) for the quickest look at the water, and go early on peak weekends. Free, open sunrise to sunset.
Rip's Rock, at Winter Clove
Moderate · ≈ 5 min driveA roughly 5-mile loop up to a cliff-top lookout over the Hudson Valley — the spot where, so the story goes, Rip Van Winkle slept twenty years. About 900 feet of climb, 2.5–3 hours.
One thing first: The trail starts on the Winter Clove Inn's private land, and they kindly let hikers through — check in at the front desk before you set off. It's the closest real hike to the house and a great half-day. Mind the edge up top.
Acra Point & the Blackhead Range
Moderate+ · ≈ 30 min driveOur favorite ridge walk. From the Big Hollow Road trailhead, take the red Black Dome Range Trail up to the blue Escarpment Trail and along to Acra Point — the big view opens up just past the summit.
Good to know: Out-and-back is about 3 miles; push on to Burnt Knob for a 6–7 mile loop if the group's feeling it. This one's a real climb — proper shoes, water, and a downloaded map, because there's no signal up there.
The Round Top trail network
Varies · on the doorstepLocally nicknamed "Roundtopia" — 20-plus miles of privately-kept trails open to the public, everything from mellow doubletrack to flowy singletrack. Walk it or bike it.
Good to know: The no-driving option for when you just want to stretch your legs near the house.
Stock the kitchen
Half the fun is what you grab on the drive in.
A few good stops for produce, eggs, flowers, and maple syrup on the way to the house.
Story Farms
≈ 15 minA fifth-generation family stand on Route 32, farming this land since 1896 — produce picked that morning, plus flowers, maple syrup, honey, jam, and baked goods. Pick-your-own berries and peas in season.
Why we love it: The classic big stock-up on the way in, and an easy stop after a hike. Open daily, roughly June through November.
Catskill Farmers' Market
≈ 20 minA seasonal outdoor market in downtown Catskill — local veg, meat, cheese, mushrooms, honey, flowers, and baked goods, plus coffee and crafts.
Good to know: Usually Saturdays through the warm months, and a nice morning outing. Times shift by season, so peek at the schedule before you go.
Black Horse Farm
≈ 25 minA big year-round country market in Athens with produce, pantry goods, plants, and flowers — the backup when the smaller stands are closed for the season.