You don’t need a week to fall in love with Ulster County — you just need a long weekend and a willingness to explore. This three-day itinerary takes you through Kingston’s revitalized waterfront, the storied hills of Woodstock, and the orchard-draped valley of New Paltz. Pack light. Leave early. The Hudson Valley is waiting.

DAY 1 — KINGSTON

Waterfront & Arts

New York’s first capital city has reinvented itself beautifully — think vinyl shops beside the Hudson, dockside oysters, and a waterfront that glows at dusk.

• Village Coffee & Goods: Start the morning here — a warm, neighborhood spot to ease into your first day

• Rhino Records: Browse the stacks at one of the Hudson Valley’s best indie record shops

• Hudson River Maritime Museum: Explore seafaring history along the scenic Rondout Waterfront

• Rondout Waterfront: Grab a dockside lunch with views of the Kingston Light

• Kingston Arts District: Spend the afternoon wandering galleries, studios, and unexpected murals around every corner

• Mariner’s Harbor: Dine like a local, then return to the marina to catch the last light fading over the river

DAY 2 — WOODSTOCK

Mountains & Music

More than a music festival — Woodstock is a living, breathing creative community tucked into the Catskills, where the air smells like pine and craft beer.

• Bread Alone Bakery: Wake up with morning coffee and a fresh pastry from this legendary local institution

• Tinker Street: Stroll Woodstock’s main drag — galleries, crystal shops, and one-of-a-kind boutiques

• Overlook Mountain: Lace up for a climb to the summit for sweeping valley views that make every step worth it

• Ashokan Reservoir: Drive through the rolling Catskills and pull over — the views demand it

• Kenneth L. Wilson Campground: Cool off at the quiet forest lake — a hidden gem for a midday swim

• Woodstock Brewing: Afternoon craft beer and spirits tasting before heading to dinner

• Cucina: Dinner at this beloved Woodstock dining staple

• Bearsville Theater: Finish the night with live music at this storied venue

DAY 3 — NEW PALTZ

History & Harvest

One of the oldest streets in America, a world-class ridge trail, and wood-fired pizza under apple trees — New Paltz is the perfect send-off for your Ulster weekend.

• Mudd Puddle Coffee Roasters: Coffee and pastries to start — a cozy local institution

• Historic Huguenot Street: Walk one of the oldest surviving streets in America, where stone houses dating to the 1690s still stand

• River To Ridge Trail: Stunning views of the Shawangunk Mountains and the valley below

• Scenic Valley Drive: Take a slow drive through the valley — roll down the windows and take it all in one last time

• Westwind Orchard: Wood-fired pizza and estate cider among the apple trees — a true Ulster County must

• Restaurant at Inness: Dinner at this acclaimed restaurant nestled on a sprawling country estate

• Arrowood Farms Brewery & Distillery: Close out the weekend with live music and a local pour

Ready to seek for yourself?

Find places to stay, eat, and explore across all three towns at visitulstercountyny.com/plan-your-visit/