Stefani Wolf Designs

Small Business Saturday is more than a day to shop; it’s a celebration of the people, creativity, and community that make Martha’s Vineyard such a special place. Each November, the Island’s charming downtowns come alive with local shopping events, holiday cheer, and the unmistakable spirit of togetherness that defines the Vineyard.

This year, Small Business Saturday falls on November 29, and across the Island, local boutiques, galleries, and specialty stores will open their doors to celebrate. Whether you are a year-round Islander or a visitor kicking off the holiday season, it is the perfect time to explore, shop, and support small businesses that help the Island thrive all year long.

Why Shopping Local Matters

When you choose to shop small on Martha’s Vineyard, you are not just checking off a holiday list; you are directly supporting the people who give the Island its unique identity. Each store, café, and gallery reflects the creativity and passion of local owners and makers. Your purchases help sustain year-round jobs, preserve the character of each town, and keep the Island community vibrant even after the busy summer months.

The Golden Ticket Program

This year, the Golden Ticket Program adds even more excitement to the holiday shopping season. Every $25 spent at participating local businesses earns shoppers one Golden Ticket for a chance to win cash prizes in a grand drawing on December 23 at The Black Dog in Vineyard Haven.

During GOLD RUSH events, including Small Business Saturday (November 29), the Vineyard Haven Celebration (December 6), and Christmas in Edgartown (December 11–14), shoppers earn two Golden Tickets for every $25 spent.

It is a fun, community-driven incentive that rewards you for doing what you already love: supporting the shops, artisans, and eateries that make Martha’s Vineyard so special.

Exploring Small Business Saturday by Town

Each of the Island’s main towns, Edgartown, Oak Bluffs, and Vineyard Haven, offers a distinct shopping experience. Whether you are searching for handcrafted art, cozy sweaters, home décor, or one-of-a-kind gifts, you will find plenty of treasures tucked into each village.

Edgartown: Classic New England Charm

Edgartown’s historic streets set the perfect scene for a day of local shopping. Stroll down Main Street, where twinkling lights illuminate storefronts and shopkeepers welcome you in.

Shops to Visit:

• Edgartown Books: A beloved independent bookstore perfect for readers and gift-givers alike. Their friendly staff can help you find local authors or beautifully illustrated coffee-table books that celebrate the Island.

Edgartown Books

• Salte and Slate: Two sister stores under the same ownership, each offering its own distinctive shopping experience. Slate focuses on contemporary women’s fashion, featuring modern, coastal-chic apparel and accessories. Salte offers a curated selection of lifestyle goods, home décor, and thoughtful gifts that reflect effortless Vineyard style.

• Backwater Trading Co.: A classic stop for Vineyard-inspired apparel and accessories for the whole family.

• North Water Gallery: Showcasing fine art, painting, and sculpture from Island and regional artists, ideal for collectors and art lovers alike.

• Vineyard Vines: While the brand has grown beyond the Island, its flagship store in Edgartown still pays homage to where it all began.

Between shops, stop into Rosewater Market for a latte or sandwich, or take a stroll down Dock Street to enjoy the harbor views before heading to your next stop.

Oak Bluffs: Eclectic, Colorful, and Creative

If Edgartown feels traditional and refined, Oak Bluffs is its playful, artistic counterpart. Here, shopping takes on a lively energy, with locally made goods, beachy boutiques, and creative galleries lining Circuit Avenue and the nearby Arts District.

Shops to Visit:

• Basics Clothing Company: Known for casual Island wear and Vineyard-branded apparel.

• Third World Trading Company: A vibrant shop offering handcrafted gifts, jewelry, and accessories from around the world.

• Craftworks: A longtime favorite for locally made and American crafts, including ceramics, glasswork, and Island-inspired ornaments.

• Stefanie Wolf Designs: A must-visit for handmade jewelry created right on the Island. Her colorful beaded designs make perfect gifts or keepsakes.

• C’est La Vie: A cheerful boutique offering home goods, Island apparel, and fun Vineyard-inspired gifts.

• Jubilee: A stylish women’s boutique featuring well-curated clothing and accessories in a welcoming atmosphere.

When it is time for lunch, head to Offshore Ale Company or Lookout Tavern, two classics within walking distance of all the great shops in town. Both are great spots to refuel before continuing your shopping adventure.

Vineyard Haven: Where Art Meets Everyday Living

Vineyard Haven is often the quietest of the main towns, but it is home to some of the Island’s most distinctive shops. It is also the heart of the Golden Ticket Program, with The Black Dog hosting the final prize drawing on December 23.

Shops to Visit:

• Bunch of Grapes Bookstore: A literary landmark known for its excellent selection and local author events.

• Citrine: A beautiful shop filled with stylish women’s apparel, accessories, and home accents.

• Rainy Day: A go-to gift and home shop known for curated items such as candles, jewelry, and Island-themed décor.

• CB Stark Jewelers: The Island’s iconic jeweler, crafting pieces that celebrate Martha’s Vineyard’s maritime heritage.

• The Green Room: A clothing and lifestyle store that offers a wide range of apparel for men and women. Its sister store, The Green Room Shoe Store, is just three doors down–together they offer clothing, surf gear and footwear, perfect for both locals and visitors.

• Conrado: A sustainable fashion boutique offering timeless, eco-friendly clothing made from reclaimed fabrics.

• 51Art Gallery: A contemporary art space highlighting the work of local and regional artists with a focus on bold, modern design.

• Chicken Alley Thrift Shop: A true Island treasure filled with vintage finds, books, and antiques, with all proceeds supporting Martha’s Vineyard Community Services.

For a bite, Waterside Market is ideal for a breakfast sandwich or hearty lunch between stores. And of course, The Black Dog Tavern remains a quintessential stop for both shopping and dining, especially during the holidays.

Up-Island: Small Town Charm and Classic Vineyard Finds

For a quieter, more rural shopping experience, head Up-Island to West Tisbury, where a slower pace and warm community spirit define the day. This is a great area to explore between scenic drives, beach walks, and farm visits.

7a Foods is a favorite stop for food lovers. Known for its creative sandwiches, baked goods, and excellent coffee, it is also a great place to pick up Vineyard-inspired gifts such as mugs and pantry treats. It is a cozy, delicious stop that fits perfectly into a day of supporting local businesses.

Just across the street, Alley's General Store stands as one of the Island's most iconic shops. It carries everything from toys and games to household essentials, souvenirs, and nostalgic candy. Stepping inside feels like visiting an old-fashioned New England general store, and it is a wonderful place to find charming stocking stuffers or simple gifts that capture the spirit of the Island.

Exploring Up-Island adds a unique layer to Small Business Saturday. Here you can experience a blend of tradition, local flavor, and easygoing Vineyard character that complements the busier downtown areas.

Beyond Shopping: Enjoying the Island in the Holiday Season

Visiting Martha’s Vineyard for Small Business Saturday also offers a chance to enjoy the quiet beauty of the Island in late fall. The pace slows, the air turns crisp, and festive decorations begin to appear across the towns.

• Light Up Oak Bluffs returns on November 29 with a full day of holiday cheer, including carriage rides, Christmas carols, a tree lighting, hot cocoa, and a special visit from Santa at The Strand. Local shops and restaurants also join the festivities with seasonal treats and specials, creating a festive atmosphere throughout town.

• The Vineyard Haven Holiday Celebration (December 6) includes music, treats, and more double-ticket opportunities for Golden Ticket participants.

• Christmas in Edgartown (December 11–14) transforms the village into a classic New England holiday postcard, complete with the lighting of the Edgartown Lighthouse.

• Cozy restaurants and cafés such as The Black Dog Water Street Bakery and Rosewater Market become gathering places where locals and visitors share stories and warmth.

Shopping small during this season connects you to the Island community in a more personal way. You are not just browsing aisles; you are meeting the people who shape the character of Martha’s Vineyard.

How to Make the Most of Small Business Saturday

• Plan your route: Focus on one or two towns to allow time to browse, enjoy coffee breaks, and chat with shop owners.

• Bring reusable shopping bags: Many Island stores encourage sustainability.

• Ask about the Golden Ticket Program: Most businesses will display a poster or mention it at checkout.

• Shop thoughtfully: Look for items made on the Island, such as Chilmark Pottery, Martha’s Vineyard Sea Salt, or locally roasted Chilmark Coffee.

• Stay for the weekend: Extend your visit to enjoy more events and earn more Golden Tickets during the following celebrations.

Small Business Saturday on Martha’s Vineyard is a reminder that supporting local businesses has a ripple effect. It keeps the Island’s towns thriving, artisans creating, and traditions alive. From Edgartown’s refined boutiques to Oak Bluffs’ artistic spirit and Vineyard Haven’s cozy storefronts, each town offers its own version of the day’s joy.

Whether you come for the Golden Ticket excitement, the thoughtful gifts, or simply to soak in the charm of a shoulder season Vineyard weekend, you will leave with something even better than what is in your shopping bag: a deeper connection to the community and the Island itself.