As the air turns crisp and the leaves hit peak color, it’s the perfect time for outdoorsy families to plan a weekend escape. Just 90 miles north of New York City, Ulster County, New York, delivers everything you need for a fall getaway: panoramic trails, eco-friendly attractions, charming small towns, and farm-to-table meals that refuel your crew after a day in the woods. Whether you’re trekking up a fire tower trail, pedaling along scenic rail tracks, or relaxing by the fireplace with a local cider, Ulster County offers the ideal blend of nature, sustainability, and comfort for a memorable family weekend.
Credit: Momtrends MediaGetting Your Feet Wet (or Muddy)
If you’re traveling with younger kids—or just easing into the weekend—start at the Catskills Visitors Center in Mt. Tremper. There’s ample parking, clean restrooms, and a beautiful, paved loop trail perfect for strollers and early walkers. This is an ideal place to get your bearings.
On the short loop trail, kids can spot bugs and birds, collect fallen leaves, and race beneath towering trees. Indoors, you’ll find interactive exhibits on the area’s ecology, along with helpful staff who can offer trail suggestions based on your crew’s abilities and energy levels. Take a minute to explore the conservation displays, especially those that spotlight the impact of invasive species and forest management practices.
Don’t miss the fire tower climb just off the main path—it’s a manageable ascent that gives even small hikers a sense of adventure and accomplishment. Be sure to grab a clipboard scavenger hunt from the front desk to keep little ones engaged along the way.
What to bring: Refillable water bottles, flat-soled shoes or sneakers.
Perfect for: Ages 0–99. ADA-accessible and stroller-friendly.
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Miles to Roam
Ready to stretch your legs a bit more? Head to the Ashokan Rail Trail, an 11.5-mile scenic route that follows a converted Ulster & Delaware Railroad line along the edge of the Ashokan Reservoir. This is one of the most peaceful, well-maintained trails in the region—ideal for walking, running, biking, or just soaking in the mountain views.
This trail is car-free and mostly flat, making it perfect for young bikers or families pushing jogging strollers. For a manageable out-and-back route, start at the Woodstock Dike Trailhead, where a paved 2.7-mile section offers wide-open views of the reservoir and Catskill High Peaks.
Families can use the trail to talk about water conservation—the Ashokan Reservoir provides drinking water to millions in NYC—and with luck, you’ll spot herons, hawks, or even the occasional eagle. Use the free downloadable birding guide from the Emerson Resort to turn your stroll into a mini science lesson.
What to bring: Sneakers or trail shoes, refillable water bottles, sunscreen. Baby carriers or wide-tire bikes are ideal for cinder sections.
Perfect for: Ages 0–99. ADA-accessible.
Credit: Momtrends MediaHiking Belleayre Mountain
If your kids are ready for a challenge, Belleayre Mountain offers a more rugged hiking experience—and big views to match. Park at the Discovery Lodge and follow the Deer Run Trail, a steep, 2-mile climb with around 1,400 feet of elevation gain. This hike will get your heart pumping, but the payoff is worth it: sweeping views of the Catskills from the summit, where you can see for miles across ridge lines and valleys.
Along the way, you’ll pass ski lift towers and construction updates, like improved HVAC systems and new accessibility features at the mid-mountain Overlook Lodge. The trail is open and wide, which makes it manageable for confident hikers ages 10 and up (or younger ones who love a challenge).
If you’d prefer a shortcut—or a ride to the top for younger family members—the Belleayre Gondola runs on fall weekends (check ahead for schedule and weather updates).
What to bring: Full water bottles, sturdy sneakers or hiking boots.
Perfect for: Ages 10+. Limited facilities—plan ahead.
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For the Rock Hoppers: Red Hill Fire Tower
For kids who love scrambling over roots and rocks, the Red Hill Fire Tower Trail is an adventurous, 4-mile out-and-back hike with about 1,200 feet of elevation gain. It’s a bit more remote, so come prepared—but families who take it on are rewarded with a fun, woodsy trail and a 60-foot fire tower climb with incredible views at the top.
Be sure to sign in at the trail register (a highlight for kids who love to feel “official”) and bring a picnic to enjoy at the summit’s grassy area, complete with a lean-to shelter and picnic tables.
What to bring: Full water bottle, long socks, sturdy hiking boots, bug spray, snacks, and a small first aid kit.
Perfect for: Ages 8+ and active families. Not stroller-friendly. No bathrooms on site.
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Home Base: Belleayre Lodge
After a full day on the trails, you’ll want a cozy place to unwind. We stayed at the Belleayre Lodge in Pine Hill—a thoughtfully renovated property just five minutes from Belleayre Mountain. The vibe is vintage-modern with plenty of Catskills character.
Each unit feels like its own little cabin retreat, with 2- and 3-bedroom options perfect for families. Expect fully-equipped kitchens, record players (instead of TVs), and playful touches like bold wallpaper and local artwork. There’s lightning-fast WiFi, but you’ll probably spend most of your downtime outside.
Onsite amenities include a fire pit, an outdoor hot tub, and a communal lodge with foosball, board games, and puzzles—ideal for keeping everyone entertained after dinner. We started each morning with breakfast in our room, using ingredients from a local farm stand, and ended each evening by the fire.
Bonus Adventures (For Rainy Days or Rest Days)
Even with the best hiking plans, the Catskills weather can throw you a curveball. Luckily, Ulster County is packed with fun, eco-conscious options for off-trail exploration.
Hudson River Maritime Museum & Solaris Solar Boat Tour
Head to Kingston for a hands-on experience at the Hudson River Maritime Museum, where exhibits explore the region’s nautical history and environmental efforts to protect the Hudson. Kids can learn about invasive species, climb aboard historic vessels, and get hands-on in the boatbuilding area.
If the weather allows, book a ride on Solaris, the museum’s 100% solar-powered boat. This quiet cruise takes you out along the Rondout Creek to the historic lighthouse once managed by Catherine Murdock, a trailblazing lighthouse keeper and mother of three.
Rough Draft Bar & Books
Warm up with cider and stories at this charming Kingston bookstore café, which encourages visitors to BYOM (bring your own mug) to reduce waste. Pick up a few reads by local authors, and don’t miss the children’s book Catskill Creatures, which celebrates the region’s wildlife.
Fabulous Furniture
In Boiceville, stop by artist Steve Heller’s Fabulous Furniture, an outdoor sculpture garden and upcycled art installation. From giant robots to retro rockets made from car parts, this is a fun and free stop that kids (and design-loving parents) will love.
Peekamoose Restaurant
For dinner, treat the family to a locally-sourced feast at Peekamoose, a Catskills institution known for its rotating seasonal menu, thoughtful cocktails, and kid-friendly touches like a reading nook and coloring pages. The towering onion rings are legendary—and never leave the menu.
Bearsville: Music, Murals, and a Little Magic
Being an art-forward destination, it’s no surprise Ulster County has a standout spot for live music. The Bearsville Theater in Woodstock is a cultural hub with deep ties to music history, offering performances for all ages across two indoor stages. While we caught a local singer-songwriter set that was more grown-up in tone, the calendar is full of family-friendly options—like the upcoming holiday tribute to Vince Guaraldi’s A Charlie Brown Christmas.
The campus includes two on-site restaurants and is known for its quirky charm—don’t miss the colorful murals in the bathrooms, which are practically a rite of passage for first-time visitors. For an easy pre-show meal, we loved Tibet Pho, just steps from the theater. The casual vibe, speedy service, and generous bowls of steaming pho make it a hit for both couples and families.
All Aboard: Rail Explorers & Scenic Train Rides
Want to keep moving without the uphill climb? Rail Explorers offers a unique, eco-friendly adventure—pedal-powered rail bikes that follow an 8-mile round-trip track in Phoenicia. Kids ages 4+ can ride, and the route is surrounded by mountain views, forested paths, and fall color at every turn.
Prefer to let the train do the work? Step back in time aboard the Catskill Mountain Railroad. Pulled by a 1950 diesel locomotive, the ride features a mix of open-air and traditional cars—so dress for the weather. Seasonal excursions include the charming Pumpkin Patch Ride and the popular Fall Foliage tour. Departures leave from Westbrook Lane Station in Kingston Plaza (with ample parking), covering a scenic 8-mile round trip. Plan to arrive at least 30 minutes before departure.
Why Ulster County Works for Outdoorsy Families
Ulster County makes it easy for families to slow down and tune in—to each other and to nature. Trails are accessible and thoughtfully maintained. Attractions center around sustainability, conservation, and creativity. And whether you’re chasing a summit or simply strolling along a lake, the pace always feels just right.
Family fall hiking in the Catskills isn’t about checking boxes—it’s about finding moments. A quiet view from a tower. A kid’s first bird sighting. A shared snack at the summit. These are the memories that last long after the leaves fall.
So pack your layers, fill up your water bottles, and head north. Ulster County is ready to welcome your crew—muddy boots, snack breaks, giggles, and all.
The post Family Fall Hiking in the Catskills: Your Weekend Guide to Ulster County Adventures appeared first on Mom Trends.
