Nestled along the Delaware River, Callicoon, New York, is a hidden gem in Sullivan County that makes for the perfect weekend escape. With its mix of small-town charm, scenic beauty, and a surprising amount of things to do, Callicoon has become a favorite destination for travelers looking for both relaxation and adventure. Whether you’re strolling through the historic downtown, sampling local flavors, or exploring the great outdoors, Callicoon offers an idyllic Catskills experience.

Friday Evening: Settle In & Stroll the Town

Arrive in Callicoon on a Friday evening and ease into your stay by checking into your homebase. Once you’re settled, take a walk through the heart of town—lined with antique shops, galleries, and welcoming eateries. Grab dinner at Rafter’s Tavern, a local favorite with live music and hearty comfort food, or opt for Callicoon Brewing Company for a laid-back vibe and locally crafted brews.

Saturday Morning: Farmers’ Market & Coffee Stop

Start your Saturday with the Callicoon Farmers’ Market, one of the largest and most beloved in the region. From fresh produce and artisanal cheeses to handmade crafts, the market captures the spirit of Sullivan County’s creative community.

After exploring the market, stop into The Kitchen Table Café for coffee and a pastry before heading down to the river. This local favorite is known for its fresh-baked goods and welcoming atmosphere — the perfect pick-me-up before a day of adventures. The Delaware River offers scenic walking spots and opportunities for kayaking, tubing, or simply relaxing on the banks with a good book.

Saturday Afternoon: Shops, Sips & Scenic Drives

Spend your afternoon exploring Callicoon’s eclectic shops. Browse vintage finds, records, and unique gifts at Spruce Home Goods or Catskill Provisions for local honey and craft spirits. For wine lovers, head to Callicoon Hills or nearby Seminary Hill Cidery in Callicoon Center, where you can sip cider while overlooking stunning orchard views.

If you’re up for a scenic drive, take Route 97 along the Delaware River for breathtaking views and photo opportunities at the Minisink Battleground Park or the famous Roebling Bridge, the oldest existing wire suspension bridge in the U.S.

Saturday Evening: Dining & Entertainment

In the evening, enjoy dinner at The Western, a beautifully restored hotel and restaurant offering seasonal menus with a modern twist. Afterward, catch a film at the historic Callicoon Theater, a charming single-screen movie house dating back to 1948 that still maintains its vintage flair.

Sunday Morning: Brunch & Farewell

Before heading home, treat yourself to a leisurely brunch. The Creek House offers a fresh, seasonal menu in a cozy riverside setting, while Peppino’s serves up classic Italian-American comfort food if you’re craving something heartier. Take one last stroll through town, pick up a souvenir or two, and maybe grab one last pastry while you soak in the laid-back atmosphere before heading back.

Why Callicoon Should Be on Your Weekend Getaway List

Callicoon strikes the perfect balance between rustic charm and modern creativity. With its riverside location, thriving food and arts scene, and welcoming community, it’s a destination that feels both timeless and refreshing. Whether you’re seeking outdoor adventure, foodie discoveries, or simply a peaceful retreat, Callicoon makes for a weekend you won’t soon forget.

Many of our properties are just a short distance to Callicoon, book with us and enjoy the best Callicoon has to offer!

A Weekend in Callicoon, NY: Small-Town Charm in the Catskills