Escape to the Southern Catskills: A Weekend Itinerary

Nestled along the scenic Delaware River, a Red Cottage rental in the Southern Catskills makes the perfect home base for a weekend escape. Enjoy cozy comforts indoors, then step outside to explore riverside towns, scenic hiking trails, local shops, and seasonal eats. With everything you need within reach, you can spend less time planning and more time savoring fresh air, small-town charm, and the simple pleasures of a Catskills getaway.

Friday: Arrival & Settling In

Settle into your Red Cottage rental and take a moment to breathe in the quiet before your weekend of adventure begins. Once your bags are unpacked, head into town to stock up on local treats and essentials for your stay.

Stop by 2 Queens Coffee in Narrowsburg for a fresh pastry and a cup of expertly brewed coffee to kick off your weekend. If you’re planning an evening in, pick up farm-made cheese and gourmet provisions from Sullivan Sundries to enjoy back at your cottage.

When it’s time for dinner, you have options: wander into The Stumble Out Bar for for inventive small plates and a fun cocktail menu, or try The Laundrette for fun flavored pizza pies and a fun cocktail menu. Wrap up the night by the fire at your Red Cottage home base, letting the river views and rolling hills set the tone for the weekend ahead.

Saturday: Adventure & Local Flavor

Wake up to a slow morning and enjoy breakfast in your cozy kitchen or stop by The Tusten Cup in Narrowsburg for a hearty breakfast sandwich or swing by J Ville Bake Shop for fresh pastries, pies, and coffee in a cozy, small-town atmosphere. With your energy topped up, it’s time to explore the natural beauty of Sullivan County.

Spend the morning hiking along the Upper Delaware Scenic Trails, where river views, forested paths, and peaceful waterfalls make every step feel like a mini adventure. If you’re craving something a little more low-key, stop by the The Catskill Fly Fishing Museum to learn about the area’s rivers, fish, and local angling history, it’s a quiet, charming way to connect with the region.

When hunger strikes, lunch options abound. Grab a hearty bite and local brews at The Catskill Brewery, or head to The Walk Inn for inventive sandwiches on house made bread. Afterward, take some time to wander local shops and galleries, stopping at Homestedt to find unique artisan gifts, home goods, and locally made treasures to take home.

As the afternoon fades, enjoy a quiet stroll along the Delaware River or a little downtime back at your Red Cottage rental. For dinner, treat yourself to something elevated: Seminary Hill, with its creative, seasonal menu and intimate setting, or The DeBruce, for an award winning culinary experience. Cap the night off fireside back at your stylish home base with a glass of wine or a cup of tea, letting the weekend’s adventures settle in around you.

Sunday: Slow Morning & Farewell

As you say goodbye to your Red Cottage stay, take the long way home on the Upper Delaware Scenic Byway and soak in one last stunning view.

Make a stop at Main Street Farm for locally made goods. Pick up fresh-baked breads, seasonal pastries, cheese, maple syrup, honey, jams, and other treats to bring a taste of the Catskills home. Let the charm of small towns and rolling hills linger as you head back, closing out a weekend that perfectly balanced adventure, cozy comforts, and local flavor.

A Weekend to Remember

Whether you’re hiking the Upper Delaware Scenic Trail, exploring Callicoon’s shops, sipping local brews at The Catskill Brewery, or relaxing fireside at your Red Cottage rental, a weekend in the Southern Catskills is pure magic. With riverside views, charming small towns, and locally made food and drinks at every turn, it’s the perfect mix of adventure, cozy comfort, and a little Catskills charm to recharge your spirit.