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Take a shady stroll along the Ashokan Rail Trail.

1. Biking and Strolling Paradise: Ashokan Rail Trail

Location: Enter at Boiceville or West Hurley Trailhead
Distance: Up to 11 1/2 miles (choose-your-own adventure)
Great For: Bikes, scooters, strollers, bird watching, scenic views
The Ashokan Rain Trail is a wide, crushed-stone path running along the old Ulster & Delaware Railroad and is one of the best flat trails in the Catskills for families. The terrain is stroller-friendly, wide enough for kids on scooters or bikes, and offers sweeping mountain views at every turn.

Eagles, deer, and wild turkeys make it a wildlife watcher’s dream. For younger children or toddlers, the flat path makes for an easy introduction to nature walks.

Good-to-Know Tip: Start at the Boiceville Trailhead for easy parking and a smoother surface. Then pop into Bread Alone Bakery nearby for organic snacks and kid-approved cookies. It’s a cozy pit stop before or after your trail time.

The Ashokan Reservoir Promenade has incredible views, 

2. A Historic Peaceful Stroll: Ashokan Reservoir Promenade

Location: Route 28A, near Olivebridge
Distance: About 5.4 miles round-trip
Great For: Toddlers, scenic walks, nature photos, gentle movement
Ashokan Reservoir is not just beautiful—it’s essential. Built in the early 1900s by engineer J. Waldo Smith, the reservoir is one of the largest in the Catskills and supplies about 40 percent of New York City’s drinking water through a 92-mile aqueduct system.

Today, families can walk along the paved Ashokan River Promenade that stretches across the dam, with breathtaking views of the reservoir on one side and the Catskill Mountains on the other. There’s a monument honoring Smith and the workers who built this massive structure by hand—a meaningful pause on your walk.

Good-to-Know Tip: Bring binoculars and turn it into a game of I-spy—count birds, find cloud shapes, or have the kids guess where the water goes! It’s educational without feeling like school.

 The Comeau Lake Trail is a fun adventure for kids!

3. A Hidden Gem in Woodstock: Comeau Lake Trail

Location: Enter the trail behind the Woodstock Pharmacy at 6 Elwyn Lane
Distance: About 1 mile
Great For: Easy hikes, waterfalls, nature play
Looking for something low-key and magical? Comeau Lake Trail is tucked away behind downtown Woodstock and offers short, shady trails leading to a peaceful lake and small waterfall. It’s perfect for curious kids—skip stones, build rock towers, and get your feet wet!

Right nearby is a small, grassy soccer field where kids can run wild before bedtime

Good-to-Know Tip: The Woodstock Library is home to a cute children's section, with a rocking horse chair, and just a stone's throw away. There's a lovely outdoor garden, bench, and table that's a perfect spot to picnic.

Photos by the author