2026 Cobblestones & Commerce

Cobblestones & Commerce: Falling for Nantucket

Join us October 9–12, 2026, for the eighth annual Cobblestones & Commerce, presented by the Nantucket Island Chamber of Commerce!

This reimagined community shopping initiative celebrates the businesses that make Nantucket special while encouraging locals and visitors to shop, dine, explore, and support local. With a fresh new look and this year’s theme, “Falling for Nantucket,” we’re bringing new energy to a favorite fall tradition—and making it more fun than ever to discover island businesses and share your favorite finds.

How It Works: Shoppers

Grab your Cobblestones & Commerce shopping bingo card and visit participating businesses throughout the weekend.

Make a qualifying purchase of $10 or more at a participating business to receive a stamp on its space. Each stamp equals one entry into our prize drawing, so the more places you visit, the more chances you have to win!

Shoppers can also earn an extra mark—and another chance to win—by sharing a photo of one of their favorite Cobblestones & Commerce finds on social media using the official event hashtag, #CobblestonesAndCommerce. Show off a new purchase, delicious bite, special promotion, or memorable local experience and help spread the word about the businesses that make Nantucket so special.

Once you have finished shopping, return your completed card to the Nantucket Island Chamber of Commerce office at 0 Main Street, Second Floor. Only qualifying purchases and social media posts made between October 9 and October 12, 2026, will count.

Follow along throughout the weekend using #CobblestonesAndCommerce, #ShopLocal, and #ShopNantucket—and get ready to fall for something new!

How It Works: Participating Businesses
 

Be part of Cobblestones & Commerce, our weekend-long celebration of shopping, dining, and supporting local!

Participating businesses will be featured through a variety of Chamber marketing and promotional efforts designed to increase visibility, encourage foot traffic, and inspire the community to shop local. To give shoppers even more reasons to visit, participating businesses are asked to contribute a giveaway valued at $25 or more (required), and offer a special promotion during the event weekend (optional).

The Chamber will also share daily “Fall for a Find” posts featuring standout products, menu items, promotions, and participating businesses. Register early for the opportunity to have your business and its offerings highlighted as part of this exciting social media series. The sooner you sign up and share your featured find, the more time we’ll have to help showcase what makes your business worth falling for!

Businesses must register by Friday, October 2, to be included on the official Cobblestones & Commerce shopping bingo card. Physical gift cards or giveaway items should be delivered to the Chamber office by 4:00 PM on Monday, October 5. Please include the details of any discounts, promotions, or featured products with your registration.

By Thursday, October 8, the Chamber will provide participating businesses with:

• Shopping bingo cards
• Official event stamps
• Cobblestones & Commerce shopping bags
• An “I’m Participating” promotional flyer

Your business and any submitted promotions will also be featured on the Chamber website and in the Cobblestones & Commerce email campaign, reaching more than 16,000 subscribers.

Visitors and locals will participate by making purchases of $10 or more at participating shops, restaurants, and businesses. Shoppers will also be encouraged to share their finds on social media, helping participating businesses gain additional visibility and creating excitement throughout the weekend.

Together, we’ll encourage island-wide exploration, celebrate local entrepreneurship, and support the businesses that keep Nantucket’s economy and community thriving.

To participate, register using the link on this page or contact events@nantucketchamber.org. Visit the Cobblestones & Commerce event page for additional information and updates.
 

Sponsorship Opportunities

Sponsorship opportunities are available for businesses looking to increase their visibility while supporting Nantucket's local economy. To learn more, email membership@nantucketchamber.org or register using the link to the right.