When the weather outside is frightful, Sullivan Catskills keeps the good times going indoors. Families swap snow boots for cozy socks and step into a weekend filled with splash-worthy waterparks, bowling showdowns, movie marathons, creative workshops, and fireside game nights.
Instead of bundling up for icy hikes, lean into hot cocoa, warm lighting and spaces designed for play, relaxation and a little family-friendly indulgence. The result feels equal parts lively and laid-back. A place where kids stay entertained, parents actually unwind and the whole weekend flows with easy, cold-weather charm.
From check-in to the final stop before heading home, this weekend follows a clear, family-friendly flow designed to keep kids entertained and moving from one fun experience to the next. The itinerary below lays out a thoughtfully paced two-day plan that balances energy, variety, and downtime, so no one gets bored or overstimulated. Each stop builds naturally on the last, keeping little ones engaged while giving parents a smooth, stress-free rhythm to the weekend.
Where to stay: Playful resort energy or quiet cabin coziness
The Kartrite Resort & Indoor Waterpark, Monticello
If your family loves built-in entertainment, The Kartrite makes a smart home base. Spacious suites give everyone room to stretch out, while the massive indoor waterpark keeps kids fully engaged from morning to night. Floor-to-ceiling windows flood the property with natural light and the overall feel balances resort ease with Catskills character.
Room service breakfasts, relaxed dining options and on-site family activities mean less planning and more time enjoying the weekend together.
Cozy cabin rentals across Sullivan County
For families craving privacy and a slower pace, cabin rentals offer another inviting option. From woodsy retreats near Callicoon to lakefront hideaways in Narrowsburg or Livingston Manor, these stays bring the Catskills indoors in the best way. Crackling fireplaces, board games stacked on vintage shelves and snow drifting gently outside the window set the scene for meaningful time together.
Think pancakes in the morning, pajama movie nights and afternoons spent reading, crafting or planning your next outing.
Saturday Morning: Big splashes and bold fun at The Kartrite
The weekend kicks into high gear inside The Kartrite Indoor Waterpark, where tropical air and turquoise slides make winter feel like a distant rumor. Kids dash toward towering waterslides like the Nor’Easter, while younger ones gravitate to splash zones designed with safety and imagination in mind. Parents float lazily in the river or unwind poolside with a coffee in hand, soaking in the playful energy.
Break for lunch at the on-site dining areas where kid-friendly menus meet relaxed, satisfying options for adults. Then dive back in for one more round before heading off to explore another side of Sullivan County.
Saturday Afternoon: Creativity, color and curious minds
1. Delaware Valley Arts Alliance, Narrowsburg
A short drive leads to Narrowsburg, where creativity pulses through small-town streets and welcoming art spaces. The Delaware Valley Arts Alliance offers rotating exhibits and family-friendly workshops that invite kids to paint, sculpt and experiment with new ideas. Hands get a little messy. Smiles grow wider. Imagination takes center stage.
2. Bethel Woods Center for the Arts, Bethel
Skip the typical craft stop and drive into deeper inspiration at the Bethel Woods Center for the Arts. Kids will enjoy exploring the museum’s hands-on exhibits: interactive displays about music, visual installations and family-friendly scavenger tours through artifacts from the famed 1969 festival site.
Meanwhile, mom and dad can take in the heritage of the legendary weekend that changed music history, exploring vinyl-era posters, stage-framed memorabilia, oral-history stations and a sweeping view of the original event grounds.
After the museum, the campus opens up for a relaxed stroll or quick café pit-stop, shifting the mood from kinetic to calm before your evening adventure. This blend of kid-friendly exploration and adult-friendly culture gives everyone something to look forward to.
Saturday Evening: Bowling, bites and a little friendly competition
1. Bowling on Broadway, Monticello
After a full day of indoor adventures, families will find lively fun at Bowling On Broadway in Monticello. This two-floor entertainment venue features 12 state-of-the-art lanes, mini-lanes specially designed for younger children, and a colorful arcade with games that appeal to all ages.
While kids roll their strikes, parents can relax in lane-side seating, easily keeping tabs on the action and enjoying a moment of ease. The on-site menu serves up casual but satisfying fare like gourmet pizza, hearty calzones, wings and fresh salads—perfect for sharing between turns without pausing the momentum of the evening.
2. Dinner Option 1: Colosseo Family Restaurant & Pizzeria, Monticello
If you prefer to sit down together and share a proper meal, head to Colosseo Family Restaurant & Pizzeria. This warm, family-friendly Italian eatery delivers the kind of comfort that feels both familiar and thoughtfully prepared. Expect generous portions of hand-tossed pizzas, classic pasta dishes and kid-friendly entrées served in a relaxed space where families can settle in and linger without feeling rushed.
Parents will appreciate the variety of menu items, from rich penne alla vodka and perfectly crisp chicken parm to seasonal specials that bring a little extra care to the table. Kids stay happy with plenty of crowd-pleasing favorites and an atmosphere that feels welcoming, unfussy and easy to enjoy after a full day of activity.
3. Dinner Option 2: Benji & Jake’s in Kauneonga Lake
For a change of scene, consider Benji & Jake’s in Kauneonga Lake. This casual, brick-oven pizzeria pairs laid-back energy with lakeside personality, creating a setting that feels both fun and distinctly local.
Families gather here over bubbling pies, shareable plates and classic comfort fare, while the relaxed dining room keeps the tone light and unpretentious. It’s an ideal spot for those who want great food, friendly service and a taste of Sullivan County’s easygoing charm all in one place.
Back at your cabin or suite, wind down with a family game night, storytelling by the fire, or a cozy movie marathon with blankets piled high.
Sunday Morning: Slow starts and cozy cafés
Piles of pancakes at Roscoe Diner, Roscoe
Sunday begins with the comforting sizzle of eggs and the smell of fresh-brewed coffee at Roscoe Diner, where they serve breakfast all day. Families settle into spacious booths while little ones dig into pancakes or French toast, and parents linger over bottomless coffee and hearty omelets. The stone-façade vintage diner vibes—classic counter seating, wood-accented touches and friendly chatter—make this a place to slow down, connect and ease gently into the end of your weekend adventure.
Sunday Afternoon: Movie magic and classic charm
A cozy cinematic finale at Callicoon Theater
Wrap up your weekend with a visit to the Callicoon Theater, an indie movie house that blends vintage style with modern comfort. Plush seating, cozy concessions and a rotating selection of family-friendly films bring everyone together for one last shared experience.
The setting feels nostalgic without feeling dated, offering a charming pause before heading home. Popcorn in hand, families settle in as the screen lights up and the weekend gently winds down.
For an added low-key option, the Ethelbert B. Crawford Public Library in Monticello often hosts children’s programs and inviting reading spaces perfect for quieter afternoons.
Indoor extras to make your weekend even cozier
- Catskills Art Space workshops for hands-on creative play
- Hands-on crafts & scavenger hunts at the Catskill Fly Fishing Center & Museum
- Family game lounges at The Kartrite
- Local farmers markets and bakeries for sweet afternoon stops
Smart tips for a seamless winter escape
- Pack swimsuits and cozy layers.
- Reserve waterpark time slots in advance.
- Check our local event calendar for pop-up workshops & family events.
- Bring a favorite family board game or two.
A weekend that feels warm in all the right ways
Sullivan County makes winter weekends easy to love. The kind filled with just enough adventure, just enough downtime and plenty of moments that feel effortless.
One minute you’re racing to the top of a waterslide, the next you’re settling into a theater seat with popcorn or lingering over pastries and hot chocolate. No overplanning. No pressure. Just a well-paced mix of energy and comfort that keeps everyone happy from check-in to checkout.
A weekend here feels like a reset button with better snacks, warmer vibes and a whole lot more fun.
