Naumkeag

10/21/2026

Get your tickets now at thetrustees.org/winterlights

10/20/2026

Something magical is brewing in our Berkshire gardens this October 🧙🏰

Bring the whole family to Naumkeag for a spell-binding evening wandering along our enchanted pumpkin trail 🍂🎃✨

Don’t miss your last chance to get discounted tickets this Wednesday (10/21) and Thursday (10/22) — we just added more tickets!

🗓️ Wednesdays-Sundays through Halloween

⏳ 4-9 pm (last entry at 7:45)

🎟️ Advance tickets required — get yours now at thetrustees.org/halloween

📍 The Incredible Naumkeag Pumpkin Show, Stockbridge, Massachusetts

10/19/2026

A little fall fun with our BTG family! 🎃 Thank you to our friends at Naumkeag and The Trustees for inviting BTG staff and their families to experience The Incredible Naumkeag Pumpkin Show. We loved spending time together surrounded by the magic of this Stockbridge tradition!

We’re also collaborating again this fall to help you enjoy both the Pumpkin Show and Summer, 1976, starring Kate Baldwin and Jennifer Van Dyck at The Unicorn Theatre through October 31.

Tickets to eligible performances of Summer, 1976 provide access to purchase discounted tickets for the Pumpkin Show’s 5pm entry on the same day. Already have your theatre tickets? Contact our box office to add some pumpkin magic to your plans! 🍂

Visit berkshiretheatregroup.org for tickets and details.

10/19/2026

Kick off the ski season at Notchview!

Three weeks till the Berkshire Trails BKL Ski Swap! See you there! ❄️

10/18/2026

🎄🖼️ A CHRISTMAS WEEKEND IN STOCKBRIDGE, MASSACHUSETTS FEELS LIKE STEPPING INTO A NORMAN ROCKWELL CHRISTMAS SCENE!

In the Berkshires, Stockbridge turns Christmas nostalgia into something you can actually walk through. Historic buildings, decorated storefronts, the landmark Red Lion Inn and the small-town Main Street create a setting that feels especially fitting during the holiday season.

The signature celebration is Stockbridge Main Street at Christmas, inspired by Norman Rockwell’s famous painting of the town at Christmastime. During the weekend, visitors can enjoy seasonal activities before the centerpiece Sunday event recreates the nostalgic Main Street scene with vintage automobiles positioned along the street.

🎄 BEST TIME TO PLAN YOUR VISIT

The celebration traditionally takes place during the first weekend of December. For 2026, Stockbridge Main Street at Christmas is scheduled for December 5–6.

While you’re in Stockbridge:

🎨 Visit the Norman Rockwell Museum
🏘️ Walk historic Main Street and see buildings connected to Rockwell’s Christmas scene
🎄 Experience Main Street at Christmas if your visit matches the event weekend
✨ Visit Naumkeag for its seasonal holiday experience
🏛️ Explore The Mission House
🏨 See the historic Red Lion Inn
🍽️ Make time for a cozy Berkshires meal

Because the signature weekend can draw larger crowds, book special programs and accommodations early and expect limited Main Street parking. Small_Town_Christmas_Escapes-NE…

For current schedules and event information, visit the official Stockbridge Chamber page.

Disclosure: Market displays, decorations, activities and event programming may vary by date and season. Small Town Discoveries is independent and is not the event organizer. Transportation, lodging, meals, attraction tickets, parking, and reservations are separate. Confirm current schedules and availability before traveling.

10/18/2026

Planning a night out at Naumkeag this fall? 🎃🍂

Make the most of your trip to our postcard perfect hometown with our guide to Stockbridge!

👉 Send this to your favs to start planning your next Berkshire adventure 📝

🅿️ Parking Zone A is in the heart of historic Stockbridge. Stroll around Main and Elm Streets (don’t miss the pedestrian lane called The Mews) before catching the shuttle to Naumkeag

🛍️ There are no chains or big box stores here, just locally-owned restaurants and shops ideal for browsing and holiday shopping
🔹 7 Arts Rare+Collectible Vinyl
🔹 An American Craftsman
🔹 BerkCHEERS Boutique
🔹 Casablanca South
🔹 Heirloom Jewelry
🔹 Nejaime’s W**e Cellars
🔹 Peace, Love & Chocolate
🔹 Sidetracks Gifts
🔹 The Shop Around The Corner
🔹 Township Four
🔹 Williams & Sons Country Store
🔹 Whispered The Heart

🍽️ Whether your dinner plans are more fine dining or deli sandwich, these local restaurants have something for you (until ~8 pm):
🔸 The Red Lion Inn: Choose between the formal dining room, cozy tavern, or speakeasy-style Lion’s Den. Reservations recommended
🔸 Once Upon a Table: A beloved bistro down The Mews known for its seasonal menus and intimate charm. Reservations recommended.
🔸 Tiffany’s Café at Elm Street Market: Neighborhood grill/deli/market great for a quick bite there or to go
🔸 Michael’s: Casual comfort food with pub vibes and a bar menu

☕️ Try these spots earlier in the day
🔸The Lost Lamb for French pastries and baguette sandwiches
🔸Main Street Cafe for breakfast or lunch set in a Norman Rockwell painting
🔸Stockbridge Coffee and Tea for a cozy caffeination break

🎭 Plan a double feature with tickets to a show at Berkshire Theatre Group (choose Parking Zone B)

🖼️ Explore more of town with a short drive to Norman Rockwell Museum, Chesterwood, Berkshire Botanical Garden, Laurel Hill Association, Stockbridge Land Trust

❓What else would you like to know about our hometown? Ask us in the comments!

10/18/2026

Stockbridge Main Street at Christmas returns December 5-6 🎄

🔗 Learn more and get tickets: stockbridgechamber.org/visit/stockbridge-main-street-at-christmas/

🎄 Tickets Are Selling for Stockbridge Main Street at Christmas! 🎄

Don’t miss the magic of the 37th Annual Stockbridge Main Street at Christmas, December 5–6, 2026! Historic Property Tours, Holiday Concert, Main Street Recreation.

Experience the charm of our quintessential New England village transformed into a festive recreation of Norman Rockwell’s beloved Home for Christmas painting.

✨ Holiday traditions, festive activities, and small-town charm await!

🎟️ Get your tickets while they last! www.mainstreetatchristmas.com

10/17/2026

🎃✨ Only two weeks left to explore The Incredible Naumkeag Pumpkin Show!

Don’t miss your chance to celebrate spooky season in our historic gardens while they’re decorated with hand-carved jack-o-lanterns and seasonal displays to delight the whole family 👻

🗓️Wednesdays-Sundays through Halloween

🎟️ Tickets sell out fast and must be purchased in advance — get yours before they disappear at thetrustees.org/halloween

📍Naumkeag, Stockbridge MA

10/14/2026

It’s that time of year when the nights get longer and our lights get brighter 🌟

We’re halfway through our Incredible Naumkeag Pumpkin Show 🎃 and just released tickets for Winterlights ❄️ which returns November 27!

Do you prefer the spooky strolls of the Pumpkin Show or twinkling trails of Winterlights? Tell us in the comments👇

👻 Limited tickets are still available for the final weeks of the Pumpkin Show — get yours before they disappear at thetrustees.org/halloween

✨ Winterlights tickets just dropped! Grab yours at thetrustees.org/winterlights

10/14/2026

🚨 UPDATE: THIS WEDNESDAY, THURSDAY & SATURDAY ARE NOW SOLD OUT ‼️

Just so you volca-know … tickets are already almost sold out for this week 🌋

Send this to a friend and start planning a lava-ly night out before the show goes dormant!

📍 The Incredible Naumkeag Pumpkin Show, Stockbridge, Massachusetts

🗓️ Wednesdays-Sundays in October 2026

🎟️ Tickets at thetrustees.org/halloween