Embrace the Festive Spirit: Explore the Holiday Activities in Lenox, MA

Have a special seasonal stay at Hampton Terrace Inn, your holiday home-away-from-home for all sorts of area activities and happenings during fall and winter. Our little slice of New England is especially sweet this time of year and provides the perfect backdrop for a luxurious and cozy retreat, far away from the hustle and bustle. There’s something for everyone, from classical Christmas traditions to spooky Halloween delights, so plan your Lenox, MA holiday getaway today before it’s too late. Keep scrolling to see everything the Berkshires has to offer with our exclusive guide; that way, you can spend less time planning and more time taking in the seasonal scenery and small-town charm.

September – October

Lenox Apple Squeeze: A Culinary Delight

One of our most exciting events, this free annual festival celebrates all things local with over 70 vendors selling handcrafted goods, beautiful art, and delectable foods, both sweet and savory! Take in the autumn atmosphere at the beer garden and listen to live music all day long with performances throughout downtown. It’s an absolute must if you’re visiting in late September, a rousing kickoff to harvest season and a thoroughly enjoyable way to spend a day in Lenox.

Lenox Tub Parade: A Quirky Experience

Originally a Gilded Age ladies’ social, the current-day parade evolved from humble beginnings and is now a yearly feature here in Lenox. Quite a quirky event to be sure, but delightfully whimsical all the same, and certainly worth attending! See citizens dressed in traditional garb and riding in “tubs” or small horse-drawn carts along with larger carriages and other surprises. It’s a unique event that adds so much to the culture of the area and is sure to make your stay here unforgettable.

Halloween Stroll at Naumkeag: A Spooky Affair

Start the spooky season off right at this incredible Halloween-themed happening running all October long! A scenic walk through the famous Naumkeag Gardens transformed into a holiday paradise with over 1,500 different carved pumpkins, themed decor, and so much more. Warm up with hot cider and munch on delicious autumn treats for sale on site, a great way to get into the spirit and support this local event. Explore the gardens to your heart’s content and see all the unique pumpkin designs, an extensive collection that showcases the incredible local talent for carving these gorgeous gourds.

November – December

NightWood at The Mount: A Hauntingly Beautiful Time

An immersive lights experience held every year at the Mount, the historic Edith Wharton home, this iconic Lenox event is a local favorite with new additions annually! Wander the ¾ mile path through magical woods and breathtaking gardens, a visual and auditory treat that celebrates the beauty of the holiday season. Be sure to dress warm and bring sturdy shoes as wintry weather may render trails a tad snowy or muddy. Also, be sure to purchase tickets well in advance as the popularity of NightWood means tickets sell out quickly!

Stockbridge Christmas: A Charming Tradition

Stockbridge was the site of one of Norman Rockwell’s most famous paintings; an idyllic Christmas scene of the village that has now inspired this annual festival. Three days of seasonal fun await, with everything from live musical performances to vintage automobiles. Get gifts for loved ones on your list at the holiday markets, take a ride in a horse-drawn carriage, or simply wander around downtown and soak up the festive atmosphere. One of the event’s most iconic showcases, Winterlights is a highly recommended visit and is sure to wow with its stunning light arrangements.

Christmas Lights at Naumkeag: An Enchanting Event

Immerse yourself in a sea of lights in this glittering winter wonderland, an annual extravaganza held at three different estates throughout the month of December. Any one of them makes for an incredible visit, with light shows held at Naumkeag in Stockbridge, the Bradley Estate, and the Steven Coolidge House. From dense woods with intimate-lit paths to expansive gardens and towering pines decked in warm holiday glow, the cozy ambiance of Winterlights is the perfect way to spend a Christmas evening in the Berkshires. Book ahead for the best chance at tickets on your preferred date and arrive early for the best parking.

A Holiday Haven at Hampton Terrace Inn

Escape the busy holiday rush at Hampton Terrace Inn and celebrate the season in charming New England surroundings. We have all the amenities to ensure your getaway is a serene stay. Whichever of our three room styles you choose to stay in, you can expect Gilded Age refinement with modern luxuries, including king and queen beds, fireplaces for cold nights, private baths, and complimentary liqueurs. Wake up to a free breakfast buffet every morning and prepare for a full day of adventures with fresh fruit, pastries, cereals, hot entrees like meat and eggs, and even more delectable options. Sip a glass of wine or Cognac by the fireplace, curl up with a good book, or play a game of chess in the living room as the snow falls gently outside. From all of us at Hampton Terrace Inn, we wish you and yours a wonderful holiday season and hope to see you soon.