Sponsored by Vermont Begins Here and Better Bennington Corporation
By Ahmad Yassir, Vermont Country Magazine.
There’s a certain magic to holiday shopping in a town that still feels like a community. In Bennington, Vermont, that magic lives in every storefront window, every handmade gift, and every shopkeeper who remembers your name. Whether you’re a holiday minimalist or an enthusiastic gifter, you’ll find that the best presents aren’t shipped in a box, they’re discovered here, crafted or curated with care, and rooted in local creativity. Shopping local isn’t just a transaction; it’s a way to celebrate relationships, support your neighbors, and embrace Vermont’s unmistakable spirit.
Antiques That Whisper History
- Covered Bridge Antiques (2026 Harwood Hill Rd, Vermont Rte 7A) is a treasure trove of vintage furniture and collectible finds.
- Stroll downtown to Main Street Antiques (473 Main St) and Monument Vintage Antiques & Collectibles (435 Main St) for a mix of classic décor, glassware, and quirky keepsakes.
Jewelry That Glimmers With Personality
Looking for something truly unique? Bennington’s artisan jewelers have you covered.
- Hawkins House Craftsmarket (262 North St) is packed with handcrafted pieces from E.L. Designs, Ed Levin Studio, plus pottery, glasswork, and Vermont-made treasures.
- Katie Cleaver (334 Main St) offers delicate sterling silver and gold jewelry that feels personal and timeless, bracelets, earrings, necklaces, all ready to dazzle your recipient.
Shops With Heart
Support local makers and give with meaning at these thoughtful boutiques:
- w.collective (198 North St) blends home goods, gifts, and antiques.
- Local & Co (434 Main St) carries jewelry, teas, toys, and décor, with many items benefiting local causes.
- Paula’s Rock Shop (126 Washington Ave) has an impressive assortment of polished stones, crystals, jewelry, tarot cards, baskets, books, and more.
Sips and Surprises
Wine lovers, rejoice! Bennington has carefully selected spots for tasting and gifting:
- Haberdasher Wine & Provisions (475 Main St)
- w.collective
- Elm Street Market (251 Elm St)
- Bennington Community Market (239 Main St)
- Powers Market (9 Main St, North Bennington)
Books to Curl Up With
Curl up with a book or find a gift for a young reader:
- Bennington Bookshop (109 South St) is Vermont’s first bookstore and a haven for literary lovers.
- Huluppu (1 Main St, North Bennington) offers cozy corners and quirky finds for every reader, with a specialty in the magical realm.
Fun for the Kids
Make little faces light up with:
- Gamers Grotto (457 Main St), Southern Vermont’s largest game store, filled with tabletop games, miniatures, cards, and more.
- Knapp’s (417 Main St) has a fun collection of toys, musical instruments, games, hobby projects, and Vermont souvenirs.
- Local & Co, Bennington Museum (75 Main St), and Jays Art Shop (115 South St) also have imaginative gifts for young minds.
Art That Inspires
Bring creativity home with:
- Jays Art Shop for art supplies, prints, original pieces, and custom framing.
- Bennington Museum and Monument Arts & Cultural Center (44 Gypsy Lane) offer art-inspired gifts alongside gallery experiences.
Specialty Foods and Treats
Local flavors are everywhere:
- The Chocolate Shoppe (471 Main St) is a chocolate lover’s dream, with handmade confections and candy galore.
- Bennington Community Market has a special holiday menu that features traditional Christmas cookies all made from scratch.
- Market Wagon (1896 Harwood Hill Rd), Haberdasher Wine & Provisions, Elm Street Market, Henry’s Market (831 Main St), Spice ‘N Nice (223 North St), and Powers Market round out a foodie’s perfect gift-hunting day.
Flowers to Brighten the Season
- The Gift Garden has been a local favorite since 1976.
- Abuela’s Plant Boutique & Flower Shop (Main St) brings greenery and blooms to every home.
Gifts Galore and One-Stop Shops
For those who love to browse, these stores have endless possibilities:
- The Gift Garden (431 Main St) and the Gift Garden’s Holiday Cottage (101 South St)
- The Local & Co
- Hawkins House Craftsmarket (262 North St)
- w.collective
- Fiddlehead at Four Corners (338 Main St, Bennington)
Experiences That Stay With You
Sometimes the best gifts aren’t things, they’re memories:
- Explore art at Bennington Museum, Left Bank (5 Bank St, North Bennington), and Monument Arts Center
- Catch live performances at Bennington Theater (331 Main St) or Monument Arts & Cultural Center
- Listen to the Basement Music Series by Vermont Arts Exchange
- Try a hands-on workshop at King’s Knit Wit (520 Main St) or Paula’s Rock Shop, or pop into classes at w.collective
- Let off some steam at Chaos (120 Depot St), Bennington’s smash room and mini arcade
Bennington is packed with discoveries at every turn, from the JK Adams display at Local & Co to the miniatures at Gamers Grotto, from fragrant flower bouquets to artisanal chocolates. Every visit is an adventure, and every purchase supports local makers and community-minded business owners. This holiday season, skip the big-box stores and experience the magic of shopping local, Bennington-style.
For more information
Downtown Visitor Center (215 South St, Bennington), and for Downtown Bennington’s official business directory, please visit BetterBennington.com
If you’re looking to explore all of Bennington, Vermont, visit VermontBeginsHere.com, the town of Bennington online travel & lifestyle guide.
