A Weekend in the Catskills

The Hudson Valley and Catskills have a way of drawing you in like that. Not all at once, but little by little, until you find yourself moving at a different pace.

Here, a good day might begin with coffee on a wide porch as morning fog lifts. It might mean a long walk down a dirt road, past old barns and stone walls, paired with a swim after the sun has warmed the hills. Or maybe it’s an evening drive as the last light fades through the rolling hills and farmland.

If slowing down sounds like how you want to spend your weekend, this two-day Livingston Manor itinerary has you covered.

Morning

Start your day with breakfast at The Walk-in, where locals line up for the café’s famously flaky square biscuits, strong coffee and breakfast sandwiches that fuel a day in the mountains. Wander Livingston Manor’s Main Street shops—design lovers should duck into Long Weekend for vintage furniture and art, Homestedt for curated homewares, and Spruce Home Goods for shelves of cheeses and kitchen goods. Source provisions at Main Street Farm, where you can grab trail snacks, sandwiches, and pantry goods sourced from local farms before heading out of town.

Late Morning

Head into the forest that surrounds the Beaverkill Valley. Hike the trails of Willowemoc Wild Forest—more than forty miles of trails weave through quiet Catskills wilderness. A favorite route links Hodge Pond and Frick Pond, a roughly 6.6-mile loop through pine forest and wetlands crossed by wooden boardwalks.

For a shorter outing, the 2.1-mile Frick Pond trail offers the same scenery in a quick hike. Download maps on AllTrails before heading out—cell service fades quickly in the woods. Fly fishing with Dette Flies—just minutes away in Roscoe, this legendary shop has been outfitting anglers on the Beaverkill and Willowemoc since the 1920s.

Afternoon

Back in town, visit Catskill Fly Fishing Center & Museum, a peaceful riverside campus dedicated to the Catskills’ deep fly-fishing history. Take a leisurely drive through the Beaverkill Valley; a winding road follows the Beaverkill River past quiet farms, covered bridges, and long trout pools shaded by hemlock. Early evening light here is especially magical. Swim or paddle at Little Pond—tucked into the forest, this peaceful mountain lake is perfect for a refreshing swim or a quiet paddle after a day of hiking. Finish out the afternoon with a stop at Catskill Art Space, Livingston Manor’s cultural centerpiece, showcasing ambitious exhibitions by internationally known artists alongside regional voices. Admission is free, though donations are appreciated and encouraged.

Evening

Return to town for dinner and drinks. There’s wood-fired cooking and natural wines at Sunshine Colony, pizza at The Kaatskeller or seafood and sidewalk spritzes at Stumble Out. For a splurge, book a table at The DeBruce, where a window-lined dining room looks out over the surrounding mountains. A nightcap at Arnold House Tavern—casual Catskills charm with a jukebox, pool table, and laid-back mountain atmosphere.

Morning

Immerse in another quiet Catskills morning before heading home. Start with the day with another visit to Main Street Farm—this time for coffee and pastries. Take your time to linger over breakfast and coffee on the porch. Next up, a Catskills fire tower hike is in store; about thirty minutes away, both Balsalm Lake Mountain Fire Tower and Red Hill Fire Tower offer beautiful forest climbs culminating in restored towers with sweeping 360-degree views.

Afternoon

One final loop through the western Catskills. Explore Livingston Manor’s more niche shops: outdoor enthusiasts can stock up on gear and gifts at Old Souls, while the nostalgic aisles of Will Hardware are packed with tools, oddities, and things you didn’t know you needed. Fashion shoppers can browse Nest or Seasons. Mine the treasures at Jitterbug, a local staple and favorite stop for families thanks to its mix of vinyl records, art supplies, toys, and games. Vintage seekers will enjoy Life Repurposed, while the gallery-like shop Corners tempts visitors with art prints, stationery, and design lit. And if you have time for the short drive to Roscoe, Taylor + Ace showcases a beautifully curated lineup of furniture and homewares.

Late Afternoon

Raise a glass before heading home with a Catskills brewery loop. Within about fifteen minutes, you’ll find several excellent options. Upward Brewing Company pairs craft beer with hiking trails and a pondside setting. Catskill Brewery is a local favorite with mountain views and frequent food trucks. Down the road, Roscoe Beer Company often hosts live music and weekend BBQs.

The Hudson Valley and Catskills are filled with houses that tell stories–century-old farmhouses restored with care, modern cabins tucked quietly into the woods, and thoughtful architectural spaces designed to frame the landscape around them. A well-placed window, a long table meant for gathering, a glowing hearth that invites you to stay just a little longer.

Bespoke rental homes from Red Cottage are chosen with that in mind—spaces that feel rooted in the land around them, where design, comfort, and landscape come together to create something lasting.

Red Cottage is the leading platform for design-driven vacation homes across the Northeast, pairing a curated collection of exceptional stays with thoughtful hospitality and high-touch services.