The Best of Berkshires Autumn Traditions at The Red Lion Inn
Giant Pumpkin Display At The Red Lion Inn
From the bright red leaves on trees to the vibrant orange gourds on doorsteps, fall colors are beginning to blanket the iconic Red Lion Inn. The charming, two-and-a-half-centuries-old Berkshires hotel offers a plethora of autumn traditions that perfectly capture the essence of fall in the mountains.
The first signs of autumn at The Red Lion Inn are unmistakable—pumpkins line the front steps, inviting guests to experience the charm of fall in the Berkshires. These cheerful gourds, with their rich oranges and yellows, serve as a warm welcome to the hotel and make a perfect backdrop for photos. Wander around the property, sip on warm cider, crunch the leaves underfoot, and take in the picturesque scenery of the Berkshires in fall. Here are some more must-experience traditions at and nearby the Red Lion Inn that will help to make up a quintessential fall weekend in the Berkshires.
Guess the Weight of the Big Pumpkin
One of the most beloved traditions at The Red Lion Inn is guessing the weight of the biggest pumpkin on the front steps. Guests are encouraged to submit their guesses for a chance to win an overnight stay for 2. Kids and adults alike take part in the guessing and competition can get fierce! (Hint: they always weigh more than you think a pumpkin could weigh!!)
Spooky Tea: A New Tradition
The Red Lion Inn is excited to bring back its Spooky Tea service, available October 24, 25 and 31, 2025. Guests are invited to enjoy a delightful afternoon tea featuring seasonal treats and spooky tea decor! With ghostly-themed pastries and a variety of teas from Harney & Sons, this unique experience is available anywhere in the hotel. We recommend requesting tea in the cozy lobby or bundling up and having it on the front porch.
Scenic Drives to Experience the Colors of Fall
One of the best ways to fully appreciate the fall foliage is to embark on a scenic drive through the Berkshires. A recommended drive is along Route 7, which winds through charming towns and showcases the stunning landscape of the mountains in fall. Starting in Stockbridge, head north on Route 7, where you’ll be greeted by a tapestry of vibrant reds, yellows, and oranges. Stop at local farms and markets along the way to pick up fresh produce and homemade goodies. Make sure to detour through the picturesque town of Lenox to admire the historic homes framed by the brilliant autumn colors.
Whether you’re visiting for a romantic getaway, a family adventure, or simply to enjoy a weekend in the Berkshires, the Red Lion Inn provides the perfect home base for exploring the region’s fall festivities. With its charming traditions, the historic Berkshires inn offers guests the chance to immerse themselves in the enchanting landscape, delicious food, and delightful activities that define the breathtaking Berkshires in fall. Book your autumnal Berkshires getaway at the Red Lion Inn!