The Ultimate NYC to Catskills Road Trip Guide 

Day 1: The Arts & Provisions

Morning: The Sculpture Trail Kick off your trip at Storm King Art Center. Wander through 500 acres of massive open-air sculptures—it’s the ultimate photo-op before hitting the mountains.

Lunch: The Local Slice Stop in Saugerties at Slices. Grab a creative, wood-fired pie at this local favorite to fuel the rest of your drive north.

Evening: The Cairo Welcome Check into Bear House Catskills and head straight to Old Factory Brewing Company. Just 5 minutes away, it’s the perfect spot for a casual first night with local craft beers.

Day 2: Craft & Peaks

Morning: The High Falls Visit Kaaterskill Falls, the most iconic tiered waterfall in New York. It’s an easy-to-moderate hike with stunning views of the Great Northern Catskills. 

Afternoon: The Modern Maker Head to Catskill Mountain Woodworking on Main Street. Meet local artisans and pick up a handcrafted, live-edge cutting board—a functional heirloom from the Catskills.

Dinner: Open-Kitchen Dining at Silvia For a truly standout meal, head to Silvia in the heart of Woodstock. Known for its open kitchen and wood-grilled flavors, this is where high-end design meets local soul. The space is stunning—think floor-to-ceiling windows and a lush, covered terrace—making it the ultimate spot for a group dinner. Their menu focuses on sustainable, farm-to-table ingredients with creative vegetable dishes and wood-fired meats that capture the best of the Hudson Valley.

Pro Tip: Reservations are a must—book at least 2 weeks in advance! 

Day 3: Style & Shopping

Morning: The Slow Brunch Wake up slow and enjoy the 2-acre grounds before heading to Gracie’s Luncheonette. They make everything from scratch—don’t skip the house-made donuts.

Afternoon: Farm Provisions Grab a jar of local honey or seasonal apples at Story Farms to take a piece of the Catskills back to NYC with you.

Final Stop: The Premium Outlets Break up the drive back to the city with a stop at Woodbury Common Premium Outlets. With 250+ designer stores, it’s the best place to find high-end home goods.