As November settles in, Bennington, Vermont, gears up for Thanksgiving, holiday shopping, and warm gatherings indoors. With an impressive selection of dining, shopping, and entertainment, Bennington offers an ideal escape for visitors looking to enjoy a touch of Vermont’s holiday spirit. Here’s your guide to making the most of a November getaway in Bennington!

Thanksgiving Reservations: A Taste of Bennington

Bennington’s restaurants and inns are a perfect way to savor Thanksgiving and early holiday meals with friends and family. Whether you’re planning an intimate dinner or a celebratory gathering, consider booking early at one of these top spots:

• Four Chimneys Inn – Celebrate Thanksgiving in this charming inn, where an elegant, cozy setting awaits.
• Madison Brewing Company – A favorite for its laid-back atmosphere, craft beers, and classic pub dishes.
• Union South – Located in the historic Putnam Block, this new venue brings fresh local ingredients and creative craft cocktails to the table.
• Publyk House – Known for its rustic New England ambiance and hearty dishes, perfect for the holiday season.
• Mount Anthony Country Club – Enjoy sweeping views alongside a delicious meal at this local favorite with a relaxed, welcoming atmosphere.
• Pangaea – The culinary gem in North Bennington, Pangaea serves inventive dishes with a focus on seasonal ingredients, offering a refined yet comfortable setting for an unforgettable meal.

See Bennington’s full list of dining destinations here. 

Early Gift Shopping: A Downtown Stroll with Unique Finds

For those looking to get a head start on holiday shopping, Downtown Bennington offers a delightful mix of shops and boutiques with thoughtful gifts for everyone on your list. The newest addition, The Haberdasher, is a must-see. With a curated selection of wines, imported goods, cheese boards, and artisanal items, it’s an aesthetic delight offering locally sourced cheeses, wine openers, and more.

Classic stops like Hawkins House and The Gift Garden continue to offer handcrafted items and local treasures, while the w.Collective and etc (located inside The Local & Co.) are perfect for finding one-of-a-kind home decor and craft items. All of these shops are within walking distance, so enjoy a leisurely stroll through Bennington’s walkable downtown while browsing unique gift ideas.

Indoor Events: Entertainment and Art This November

November marks the start of indoor programming and events in Bennington, giving locals and visitors an abundance of cozy entertainment options.

The Coffee Bar Music Series kicks off, featuring live performances that provide a warm, intimate backdrop for chilly evenings. In Downtown Bennington, The Bennington Theater has announced its new season, bringing together children’s, professional, and community theater performances. Their lineup includes everything from theater to comedy and live music, attracting nationally touring artists and performers.

For something unique, try Trivia Night Live at The Bennington Theater, which blends theatrical elements with classic trivia for an immersive, unforgettable experience every second Thursday of the month. Also, the theater’s New Works Series offers in-house readings that provide a behind-the-scenes look at unproduced plays and performances.

Bennington Theater’s upcoming events include: November 1 – Forever Simon & Garfunkel: A Tribute, an evening celebrating the timeless music of Simon & Garfunkel.

Panto Company USA Presents: Rumplestiltskin! on November 15, a delightful take on the classic fairy tale, perfect for families. If you miss one of these, don’t worry—Bennington Theater will have many more productions coming up! 

Over on the west end of town, the Monument Arts & Cultural Center hosts its 2024 Holiday Invitational starting November 1st, with an opening night featuring live music in the lobby and drinks by South Shire. 

This annual event showcases works from renowned artists such as Ann Larsen, Corey Pitkin, and Eden Compton, creating a gallery experience filled with holiday cheer. Visitors can also enjoy a full schedule of performances throughout the month:

• November 1 & 2 – A sold-out art workshop with artist John McDonald (waiting list only).
• November 3 – Music in the lobby by Brian & Suzy Hanner with refreshments by South Shire Inn.
• November 10 – Live music by Julie Shea, a celebrated local talent.
• November 14-17 – Million Dollar Quartet, a must-see musical production (tickets available at Monument Center).
• November 23 – Metropolitan Opera star Oren Gradus performs an evening of Broadway and more, promising an unforgettable night of music (Tickets).

Be sure to explore the Monument Arts Gift Shop, which has a delightful selection of handcrafted gifts, local art, and collectibles. Don’t miss the Covered Bridge Museum and Portals of the Past exhibit for a dive into Bennington’s rich history.

The Bennington Museum adds to the rich November lineup with special programs that celebrate art, history, and live music. Enjoy these engaging events throughout the month:

• November 2 | 2:00 pm – 3:30 pm
  Finger Lakes Guitar Quartet
  Part of the Music at the Museum series, this performance brings an afternoon of beautiful guitar music to the museum.
• November 17 | 2:00 pm – 3:00 pm
  Edith Roosevelt Comes to Bennington: A Vermont Tourist in the Gilded Age
  Step back in time with this historical presentation on Edith Roosevelt’s travels and experiences as a tourist in Vermont during the Gilded Age.
• November 26 | 4:30 pm – 6:30 pm
  Uncanny Valley – Artist Reception
  This artist reception offers a first look at the Uncanny Valley exhibit, with a chance to purchase artwork during the “BUY IT NOW” opportunity. Admission is free to $5.00, making it a perfect evening for art enthusiasts.

These events offer a cultural touchpoint for visitors looking to dive into Bennington’s history, art, and music in a beautifully preserved setting. For tickets and details, check the Bennington Museum website or visit in person to explore exhibits and gift shop finds.

Bennington in November brings together everything that makes the season special—warm meals, unique gifts, and plenty of live entertainment—all set against the charming backdrop of a town ready to welcome visitors for the holidays. Make Bennington your holiday destination this November and embrace the warmth of Vermont hospitality.