After a busy start to the school year, we were more than ready for a quick fall escape from NYC. Our summer road trip to Acadia felt like a distant memory, and we were itching to hit the road again—this time to see the changing leaves in upstate New York.

We picked Hunter as our destination. While it’s known as a ski town, it turns out that Hunter is also perfect for a fall family weekend in the Catskills. The weather was gorgeous, the foliage was at its peak, and fall festivals added a festive touch to the whole experience. Here’s how we spent our long weekend:

Day 1 – Arrival and Hot Tub Views

We left the city in the afternoon right after picking up the girls from school, and by the time we arrived at our rental, there was still enough daylight to enjoy the deck and the view. We didn’t even unpack—just rushed out to soak in the golden light and relax in the hot tub with the mountains and village as our backdrop.

Dinner: We kept it simple with dinner at Mama’s Pizza and Trattoria. The food was fresh, and Italian always works for our family since some of us are vegetarian.

Day 2 – Rail Explorers, Phoenicia Diner, and Kaaterskill Falls

We kicked off the day with a family ride at Catskill Rail Explorers. We chose the 2.5-hour River Run Tour, where we pedaled a quad bike along the historic Ulster & Delaware Railroad. The path follows the Esopus Creek and winds through the forest—such a beautiful and fun way to take in the scenery.

This was one of our favorite activities from the trip. It was the perfect mix of fresh air, light movement (not too physically demanding), and quality time. It’s also something you can enjoy with young kids or even grandparents. We booked it in advance, which I highly recommend—it fills up quickly. (Good to know: cancellations made more than 48 hours ahead are fully refundable.)

Lunch: Right after the rail experience, we headed to Phoenicia Diner, which is just around the corner. Since the diner was packed, we opted for their food truck outside and ate in the open-air seating area called The Lot. It was casual, easy, and delicious.

Next, we drove to Kaaterskill Falls, one of the most iconic waterfalls in the region. There are a few ways to see the falls—you can view them from above with just a short walk from the parking lot, or you can hike down to the base, which is about 300 feet in elevation (easier down than up!). We did both: first, all of us walked to the overlook. Then my husband and I took the trail down to the base while the girls waited at the top. The hike was absolutely worth it.

Day 3 – Belleayre Fall Festival and Ashokan Rail Trail

We started our day at Fred’s Coffee and Donuts, a spot we noticed the day before thanks to its long line. Turns out, the donuts are amazing—and the setting is just as sweet, with panoramic mountain views.

Next up was the Belleayre Fall Festival. The drive from Hunter was beautiful, and when we arrived around noon, the main parking lot was already full. Luckily, everything was well-organized, and we easily caught a shuttle from a nearby overflow lot. The festival was full of energy: live music, food trucks, cider, and a laid-back crowd enjoying the sunshine. The highlight for us was taking the gondola to the top of the mountain—clear skies, crisp air, and those views!

Later in the afternoon, we were ready for a bit of quiet and movement, so we headed to the Ashokan Rail Trail. This scenic 11.5-mile trail runs along the Ashokan Reservoir and follows the old Ulster & Delaware Railroad. There are three main trailheads to choose from. We started at the Boiceville Bridge Trailhead, which is ideal if you want sweeping views of the reservoir. We only walked a portion of the trail, but it was a peaceful way to unwind, and we crossed paths with plenty of locals out for their daily stroll or walk with their dogs.

Day 4 – Hunter Oktoberfest and Back to the City

Before heading home, we stopped by the Hunter Oktoberfest. It had a similar vibe to the Belleayre Festival—live music, good food, and a festive crowd. We had lunch there, listened to a local band, and bought a couple of beautiful bracelets made by a local artist.

It was a short vacation, but exactly what we needed: a chance to slow down, breathe in some mountain air, and enjoy fall in the Catskills together as a family.

Where to Stay

Scribner’s Catskill Lodge – part of Design Hotels. This 38-room lodge has that perfect mix of rustic and modern. It sits on 20+ acres with gorgeous views of the Hunter Mountains. On-site you’ll find Prospect restaurant and bar, a cozy library, pool, sauna, outdoor decks, a kids’ corner, and even a fire pit for s’mores. A great pick for families, couples, or friends traveling together. And just a little tip: if you book Scribner’s through me, you’ll get extra perks like free breakfast and possible room upgrades — all at no added cost.

Looking for more family travel inspiration? Take a look at our 10-Day Family Itinerary from Rome to the Amalfi Coast or explore our favorite Top 5 Things to Do in London with Teenagers. Ready to start planning your next family getaway? I’d love to help—feel free to reach out to me here or sign-up for our newsletter.