Experience the Best of Fall Foliage at the Stephentown Hotel: A Perfect Weekend Getaway
As the crisp autumn air settles in and the leaves begin to change, there’s no better time to plan a weekend escape to the Stephentown Hotel. Nestled in the foothills of the Berkshire Mountains and just a stone’s throw from the New York/Massachusetts border, the Stephentown Hotel offers the perfect base for an unforgettable fall foliage adventure. Whether you’re into hiking scenic trails, visiting local cider mills and orchards, or sampling craft brews, there’s something for everyone to enjoy. And with special amenities like firepits, S’mores packages, and arcade games in every apartment, your stay will be as cozy as it is fun!
Day 1: Arrival and Local Cider Tastings
Start your weekend by checking into the Stephentown Hotel, where you’ll be greeted by comfortable accommodations perfect for families, couples, or groups of friends. Each apartment comes with arcade games to keep everyone entertained, while the firepits (complete with firewood and fire starter) offer the perfect opportunity to gather around in the evening. And to make your night even sweeter, we provide a S’mores package with every stay—so you can roast marshmallows under the starry sky and fully embrace the fall experience.
After settling in, head out to explore the local cider scene. A short drive away, you’ll find Brookview Station Winery, which is known for its award-winning hard ciders made from locally grown apples. Sip on seasonal favorites like crisp apple cider or a spiced variety, and soak in the vibrant fall colors while relaxing outdoors.
For dinner, try S&S Farm Brewery just down the road. This family-run brewery features craft beers brewed on-site using ingredients from their own farm, and their cozy taproom is the perfect place to enjoy a pint and a hearty meal made with local ingredients.
Day 2: Scenic Hikes and Orchard Visits
Rise and shine for a day filled with breathtaking fall scenery! Start your morning with a hike at Cherry Plain State Park, just a short drive from the hotel. The park offers a variety of trails, ranging from easy walks to more challenging hikes, all with spectacular views of the changing foliage. Don’t forget your camera — the views from the hilltops are stunning at this time of year.
After your hike, head to Love Apple Farm, where you can pick your own apples and pumpkins or browse the farm’s market for fresh produce and homemade pies. The orchard is a great spot to grab a picnic lunch to enjoy under the colorful autumn canopy.
Next, swing by Goold Orchards, where you can continue your apple-picking adventure or indulge in some cider donuts and warm apple cider. The farm also has a distillery on-site, so you can try a sampling of apple spirits before heading back to the hotel.
Evening Relaxation: Firepit Fun
Back at the Stephentown Hotel, gather around one of the firepits to end your day on a relaxing note. With firewood and fire starters provided, you can easily build a fire and enjoy an evening roasting marshmallows with your complimentary S’mores package. The crisp fall air, the warmth of the fire, and the sight of the vibrant foliage surrounding the property will make for a perfect autumn evening.
Day 3: Brewery Tour and Scenic Drive
Before you check out, plan a leisurely drive through the countryside to experience the full splendor of the fall foliage. The winding roads around Stephentown and nearby towns like New Lebanon and Hancock offer some of the best scenic routes in the region. Along the way, stop at Chatham Brewing, a local favorite offering a range of seasonal beers, from hoppy IPAs to rich stouts.
If you’re in the mood for one last adventure, consider a hike at Jiminy Peak Mountain Resort, located just 7 minutes from the hotel. While primarily known as a ski resort, the trails here are open year-round and provide incredible views of the valley below.
Why Stay at the Stephentown Hotel?
The Stephentown Hotel is the ideal place to stay for your fall foliage weekend getaway. The hotel’s unique setup—four private apartments with ample space for families or groups—ensures a comfortable and memorable stay. Plus, each apartment features fun arcade games, perfect for winding down after a day of outdoor adventures. And with firepits and S’mores packages included with every stay, your fall evenings will be filled with warmth and relaxation.
With weekly discounted rates available for fall travelers, you can enjoy a longer stay and fully immerse yourself in everything this beautiful region has to offer. Whether you’re planning a romantic weekend for two or a group trip with friends, the Stephentown Hotel is ready to welcome you for a fun-filled fall foliage weekend!
Book your stay now and get ready for an unforgettable autumn adventure. Checkout our nearby page for a list of nearby activities, adventures, restaurants, breweries, orchards, etc.
