As a mom who raised two kiddos in Brooklyn, I can tell you: the need to “touch grass” is real (no matter the weather). Little kids need space to roam, get messy, and connect with nature. The good news? Planning that outdoor time doesn’t have to be complicated—Ulster County has itineraries that fit every kind of family.

Fall hiking trips don’t have to involve extreme challenges, tons of gear, or loads of ambition. The Catskills offer a range of trails—from stroller-friendly paths to vertical climbs—making it easy to find something that fits your family’s vibe. And if you pick Ulster County as your destination, it comes with the added bonus of cozy lodging and great restaurants and making it the perfect home base after each outdoor adventure. In this moment of seasonal anticipation (come on snow!), these fall hiking weekends are a great way to get your family moving outside and invested and interested in the change of seasons.

Planning Made Easy
If you are the travel agent in your family, I want to help you take a big exhale. A hiking trip is an EASY one to pull off (especially compared to skiing). Start your planning at visitulstercountyny.com. Ulster County is home to more than 35 peaks and 350 miles of trails all you really nee to book is your home base and the rest you can figure out once you arrive—no lift tickets, lessons or reservations required.

On a recent fall trip, I set a goal: find four types of hikes. I wanted a few challenges and some chill walks where the scenery was the point—not the workout. For my latest fact-finding mission in the mountains, I grabbed a girlfriend and my hiking boots for a two-day trip. In 48 hours, we tackled four hikes with varying difficulty to show that there truly is something for everyone here.

Home Base
I stayed at the wonderfully renovated Belleayre Lodge (15 Hostel Dr, Pine Hill, NY, United States), just five minutes from Belleayre Mountain. Under relatively new ownership, the lodge went through a full refresh four years ago. Families will love the 2–3 bedroom options, complete with kitchens and plenty of space to spread out.

Each morning started with whipping up a hearty breakfast in our little kitchen (with farm-fresh goodies from Migliorelli Farm Stand) before hitting the trails. Every unit has its own personality—think vintage finds and quirky wallpaper. What you won’t find? Screens. Instead, each unit comes with a turntable and a few vinyl records. (Don’t worry—there’s lightning-fast WiFi for trail maps.)

Onsite perks include an outdoor hot tub, fire pit, and a big communal lodge—perfect for board games, foosball, or relaxing with a puzzle after a day outside.

Getting Your Feet Wet (or Muddy)

For families with little ones, start at the Catskills Visitors Center (5096 NY-28, Mt Tremper, NY 12457). There’s a large parking lot, and everything is stroller- and wheelchair-friendly. Start your visit on the paved loop trail, spotting bugs, birds, and trees.

Then pop inside to explore the exhibits (and enjoy the very clean bathrooms). Staff can help with trail suggestions and share fun facts about the region’s ecology. Check out the conservation displays to learn about invasive species, and don’t forget to grab a scavenger hunt clipboard for the kids.

With 1.5 miles of gentle trails and the chance to climb a fire tower, it’s a great way to kick off your Catskills experience.

What to bring: Refillable water bottle (there are fountains inside), sneakers or flat-soled shoes.
Perfect for: Ages 0–99. ADA-accessible trails.


Miles to Roam
If you are looking to log more steps, your next stop should be the Ashokan Rail Trail. This 11.5-mile, flat trail follows a former Ulster & Delaware Railroad line that once served the region’s resort towns. Now, it hugs the edge of the Ashokan Reservoir, which provides drinking water to NYC—so no boating, but it’s perfect for walking, biking, and bird watching. Speaking of birding, you can download a FANTASTIC digital guide to the birds in the area courtesy of the Emerson Resort here. While we didn’t see any eagles, we did spot a few herons and kids will love using the guide to get some fun facts about the feathered friends they see.

I ran a 5-mile stretch with my buddy under a canopy of fall color, stopping often to admire the views. For young families, I suggest heading to the Ashokan Rail Trail Promenade at the Woodstock Dike Trailhead (1285 NY-28, West Hurley, NY). This 2.7-mile paved section is stroller-friendly, accessible, and lined with scenic water views. This section is much more exposed and offers the chance for families to talk about clean water and our motivation to keep it that way.

What to bring: Sneakers or flat-soled shoes, refillable water bottle, sunscreen. For the cinder sections, use a baby carrier or bikes with wide tires.

Perfect for: Ages 0–99. ADA-accessible trails.



After Some Vertical?
For older kids who love a challenge, try hiking Belleayre Mountain (181 Galli Curci Road, Highmount, NY 12441). Known as one of the most popular ski areas in New York, Belleayre is part of ORDA (the Olympic Regional Development Authority), which also manages Whiteface and Gore. That means there is load of terrain and some steep inclines—so be ready for a workout.

Park at the Discovery Lodge, then follow the Deer Run Trail, a 2-mile hike to the summit at 3,429 feet with an elevation gain of about 1,400 feet. My kids always loved imagining what the slopes look like in winter and my friend and I were hatching plans to come back and ski as we hiked the steep ski trails. Along the way, we spotted updates being made to the mid-mountain Overlook Lodge—improving HVAC and accessibility.

At the summit, congratulate your crew with a snack as you plan your winter ski routes. From the top, enjoy sweeping views of the Catskill High Peaks, rolling ridge lines, and deep forested valleys that stretch for miles. If the full hike feels like too much, the gondola runs on fall weekends, offering a ride to the top (the dates and times of the rides vary so check the Belleyare website to make sure it’s running).
What to bring: Full water bottle, sturdy sneakers or hiking boots.

Perfect for: Kids 10+, or adventurous younger ones up for a partial hike. Limited facilities, so plan ahead

Getting into Nature
For kids who love rocks, roots, and streams, the Red Hill Fire Tower hike is a must. Park at the DEC parking lot and set off on a 4-mile out-and-back trail with a steady 1,200-foot elevation gain. Be sure to sign in at the beginning of the trail and out at the end (by the way kids LOVE this and the box that holds the sign in sheets—they really feel like explorers).

This intermediate hike has uneven terrain and plenty of opportunities for kids to explore (and you’ll probably see some deer or other wildlife). The reward? A 60-foot climb to the top of the fire tower, plus a grassy area with picnic tables and a shelter.

What to bring: Full water bottle, sturdy hiking shoes, long socks, bug spray, sunscreen, snacks, and a first aid kit.

Perfect for: Ages 8+. Not accessible for strollers or those with disabilities. No bathrooms—plan ahead.

Hey, Just What Is a Fire Tower?
Two of the hikes I mention here feature fire towers—tall, steel structures rising above the trees. Built in the early 1900s, fire towers were used by forest rangers to spot wildfires before satellite surveillance existed. Rangers would climb into the cab (the little room at the top) and scan the landscape for smoke.

Today, they’re no longer used for fire-spotting, but they’ve become beloved hiking destinations. With 360-degree views and a touch of history, they’re a fun reward at the end of a climb.

Your family might even want to take on the Catskills Fire Tower Challenge—visit all six of the towers in the area between Jan. 1 and Dec. 31, 2025. Learn more at: dec.ny.gov

Final Thoughts
This corner of New York, just outside the city, is a perfect gateway for families who want to explore nature with a soft landing. Ulster County is full of opportunities to slow down and reconnect outdoors. Even if you can only manage an overnight trip, it’s a beautiful way to let your kids experience what it means to truly connect with the natural world.