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Catskill Mountains, New York: Where to Stay, Where to Play, and What to Eat. A 4 day Itinerary for Adventurous Families.

Updated: 2 days ago



The Catskills region in New York is one of our favorite places to visit all year round. Especially perfect for outdoor loving families: think endless mountain views, cascading waterfalls, and a whole lot of adventure packed into over 700,000 acres of wilderness. It's the best destination for families craving a perfect mix of relaxation and excitement in the great outdoors. Time to pack your bags and get ready for a Catskills mountain escape!




Where to stay: Winter Clove Inn


The Winter Clove Inn serves as the perfect base for your Catskills autumn adventure, offering a blend of comfort, history, and on-site activities. This charming, family-owned inn has been welcoming guests since 1838, making it one of the oldest continuously operating inns in the Catskills.

Set on 300 acres of private land, this all inclusive inn provides a unique mix of natural beauty and recreational facilities. Guests can enjoy:

  • On-site hiking trails, including a path to the picturesque Artist Falls

  • Indoor and outdoor pools

  • Tennis courts, basketball court, and volleyball area

  • 9-hole golf course (complimentary for guests)

  • Game room with pool table, ping pong, and board games

  • Fitness center

  • Three hearty meals a day included in the room rate

  • Nightly entertainment, including bonfires and live music

  • Wi-Fi throughout the property


The inn's main building features a cozy living room with a fireplace, perfect for relaxing after a day of exploration. In the fall, the surrounding forest bursts into a spectacular display of autumn colors, making the inn's wraparound porch an ideal spot for leaf-peeping.



Where to play:

  1. North-South Lake: Hiking trails, lake views, and stunning vistas

  2. Zoom Flume: New York's #1 Family Amusement and Outdoor Water Park

  3. Hunter Mountain Scenic Skyride: Take a chairlift to the summit for panoramic autumn views

  4. New York Zipline Adventure Tours: Experience the fall colors from above on North America's longest and highest zipline canopy tour

  5. Howe Caverns: Explore underground caves and try rock climbing or spelunking

  6. Catskill Mountain Railroad: Scenic fall foliage train rides

  7. Mountain Top Arboretum: Treetop rope course and canopy walks among fall foliage

  8. Windham Mountain Bike Park: Downhill mountain biking with trails for all skill levels

  9. Hudson River Skywalk: A pedestrian walkway connecting two historic sites with stunning views




Best Hikes:

  1. Easy: Artist's Rock via the Escarpment Trail in Hunter, NY (2.0 miles round trip, elevation gain: 250 feet)

  2. Moderate: Kaaterskill Falls Trail (1.4 miles round trip, elevation gain: 420 feet)

  3. Challenging: Devil's Path to Indian Head Mountain (6.6 miles round trip, elevation gain: 2,200 feet)




Where to eat:

  1. Winter Clove Inn Dining Room: On-site dining with family-style meals featuring locally-sourced ingredients and traditional Catskills cuisine.

  2. Circle W Market: A charming general store offering top-tier sandwiches, local products, and homemade baked goods. Perfect for picking up hiking fuel.

  3. Mama's Boy Burgers: A retro-style burger joint in Tannersville known for its delicious grass-fed beef burgers, hand-cut fries, and creamy milkshakes.

  4. Willa's: A cozy breakfast spot in downtown Catskill serving up hearty morning fare with a focus on local ingredients and homemade pastries.

  5. Subversive Malting + Brewing: A craft brewery and taproom offering unique beers brewed with locally-grown and malted grains, along with a menu of pub-style foods.

  6. Texas Weiners: A local institution since 1925, famous for its hot dogs topped with a secret chili sauce recipe.

  7. Ambrosia Diner: A classic American diner offering a wide range of comfort foods, from all-day breakfast to Greek specialties.

  8. The Salad Bar: A health-focused eatery providing fresh, customizable salads, grain bowls, and smoothies for the nutrition-conscious traveler.



Best Photography Spots:

  1. Artist's Rock: Panoramic views of fall foliage in the Hudson Valley

  2. North-South Lake: Stunning lakeside vistas with autumn reflections

  3. Thomas Cole National Historic Site: Capture the landscapes that inspired American art in fall colors

  4. Downtown Catskill: Charming streetscapes and the "Cats of Catskill" outdoor art exhibit

  5. Hudson River Skywalk: Breathtaking views of the Hudson River and surrounding fall landscapes



Homeschooling/Learning Resources:

  1. Thomas Cole National Historic Site:

    • Guided tours of Cole's home and studio (45 minutes)

    • Art-making workshops inspired by Hudson River School techniques (2 hours, suitable for ages 12+)

    • Junior Ranger program for kids (free activity booklet)

  2. Olana State Historic Site:

    • Landscape painting workshops (3 hours, all skill levels)

    • Historic landscape tours (1.5 hours)

    • Family-friendly scavenger hunts around the grounds

  3. Mountain Top Arboretum:

    • Guided ecology walks (1 hour, learn about local flora and fauna)

    • Tree identification workshops (2 hours, suitable for ages 10+)

  4. Catskill Interpretive Center:

    • Interactive exhibits on Catskills ecology and history

    • Guided nature walks with park rangers (1 hour)

    • Leave No Trace outdoor ethics workshops (45 minutes)



Our 4 Day Itinerary:

Day 1:

  • Arrive at Winter Clove Inn in Round Top, NY

  • Explore the property: Enjoy a fall nature walk, play pickleball, shuffleboard, or tennis

  • Take a short hike to Artist Falls on the property to see the autumn colors

  • Dinner at Winter Clove Inn

  • Enjoy live local music and barbecue provided by Winter Clove Inn

Day 2:

  • Breakfast at Winter Clove Inn

  • Pick up hiking fuel at Circle W Market

  • Hike at North-South Lake (choose from Easy, Medium, or Challenging trails) to enjoy fall foliage

  • Late lunch at Mama's Boy Burgers in Tannersville

  • Visit a local apple orchard for apple picking and cider tasting

  • Return to Winter Clove Inn for dinner

  • Attend the guest bonfire at Winter Clove Inn, complete with s'mores

Day 3:

  • Enjoy a relaxed morning at Winter Clove Inn (coffee on the porch overlooking fall colors, 9-hole golf game, or short hike to Artist Falls)

  • Breakfast at Willa's in downtown Catskill

  • Visit the Thomas Cole Museum to see how fall inspired the Hudson River School painters

  • Walk across the Hudson River Skywalk for panoramic autumn views

  • Late lunch in downtown Catskill (choose from Subversive Malting + Brewing, Texas Weiners, Ambrosia Diner, or The Salad Bar)

  • Explore downtown Catskill:

    • Outdoor Art Exhibit - The Cats of Catskill

    • Kirwan's Game Store

    • Spike's Record Store

    • Dutchman's Landing Park for riverside fall colors

  • Dinner at Winter Clove Inn

Day 4 (Departure):

  • Breakfast at Winter Clove Inn

  • Hike Kaaterskill Falls Trail

  • Head home and plan your next trip back


Trust me, the Catskills are something special – where else can you zip through colorful treetops, hike to jaw-dropping views, and walk in the footsteps of famous artists all in one trip? It's the perfect spot for families looking to mix outdoor fun with a bit of learning, all while soaking in some seriously beautiful scenery. Whether you're chasing waterfalls, trying your hand at fly fishing, or just relaxing in a cozy inn, the Catskills have a way of creating those "remember when" moments that'll keep you coming back for more.

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