Waterfalls, Wineries, and Wonder: The Ultimate Catskills Getaway

The Catskills are calling, and if you’re looking for a weekend full of adventure, relaxation, and a little bit of magic, The Roxbury is the perfect home base. Whether you’re chasing waterfalls, sipping on local wines, or simply soaking in the whimsical atmosphere of our one-of-a-kind hotel, this itinerary will help you make the most of your getaway.

Day 1: Arrival & Immersion in Whimsy

Check-in at The Roxbury

Your adventure begins the moment you step into The Roxbury. Whether you're staying in one of our iconic themed rooms or indulging in a tower cottage experience, get ready to be transported into a world where fantasy meets luxury. Drop your bags, snap some Instagram-worthy pics, and get ready to explore!

Dinner & Drinks at Peekamoose Restaurant & Tap Room

After settling in, head over to Peekamoose Restaurant & Tap Room, a beloved Catskills staple that focuses on farm-to-table dining. Enjoy locally sourced dishes and creative cocktails in a cozy, rustic atmosphere.

8373 NY-28, Big Indian, NY

Stargazing & S’mores

End your first night under the stars! The Catskills have some of the best stargazing in the Northeast. Grab a glass of wine, cozy up by an outdoor fire pit, and let the fresh mountain air set the tone for the rest of your getaway.

Day 2: Waterfalls & Wineries

Morning: Kaaterskill Falls Hike

Start your day with a short road trip to Kaaterskill Falls, one of the most stunning waterfalls in the region. A relatively easy hike rewards you with a breathtaking, two-tiered waterfall cascading down 260 feet—perfect for nature lovers and photographers alike.

Route 23A, Haines Falls, NY

Pro Tip: Get there early to beat the crowds and enjoy the falls in peaceful serenity.

Afternoon: Wine Tasting at The Vineyard at Windham

After a refreshing hike, it’s time to unwind with a little wine. The Vineyard at Windham offers picturesque views and a curated selection of locally crafted wines. Sip on a crisp Riesling or a bold red as you take in the rolling Catskills landscape.

11 Mount View Estates Rd, Windham, NY

Evening: Relax & Rejuvenate at The Roxbury

Back at The Roxbury, it’s time to pamper yourself. Book a spa treatment, take a dip in the hot tub, or simply relax in your uniquely themed room. Whether you're sleeping under a giant chandelier in The Final Frontier or feeling like royalty in Cinderella’s Gown, every room at The Roxbury is its own escape.

Day 3: Brunch & Boutique Shopping

Brunch at Phoenicia Diner

Before heading home, treat yourself to a hearty brunch at the Phoenicia Diner. Known for its retro vibes and incredible farm-fresh meals, this diner is a must-visit. Their skillet breakfasts and fluffy pancakes are the perfect way to cap off your trip.

5681 NY-28, Phoenicia, NY

Explore Local Shops & Art Galleries

Before you say goodbye to the Catskills, take a leisurely stroll through Tannersville or Woodstock, where you’ll find unique boutiques, art galleries, and quirky souvenir shops. It’s the perfect way to take a piece of the Catskills home with you.

Final Thoughts

A weekend in the Catskills is all about balance—thrilling outdoor adventures, indulgent relaxation, and, of course, a touch of whimsy when you stay at The Roxbury. Whether you're hiking to waterfalls, sipping wine in the mountains, or simply escaping reality in a themed suite, this region offers something truly special.

Ready to experience the magic for yourself? Book your stay at The Roxbury and start planning your own unforgettable Catskills adventure!