Could Cobblestones & Commerce Be Your Reason to Visit Nantucket for Local Shopping This Fall?

09/14/2026

Fall is one of the best times to be on Nantucket, and this October, there’s another great reason to plan a visit. As a follow on to Restaurant Week being announced, The Nantucket Chamber of Commerce is also bringing back Cobblestones & Commerce, a community shopping event taking place October 9-12.

Cobblestones & Commerce Explained

Cobblestones & Commerce is a local shopping event native to Nantucket, and it’s a great way to experience the island beyond the traditional summer season and support the local businesses that make Nantucket so special.

The way it works is that shoppers are encouraged to pick up a shopping bingo card at a participating business, or the Chamber of Commerce office at Zero Main Street. From October 9-12, you can visit the participating shops and spend at least $10 to receive a stamp on your card.

Essentially, the more places you shop, the more chances you have to win! Each stamp counts as one chance to win prizes, and completed cards can be dropped off at the Chamber office at Zero Main Street, 2nd Floor.

A full list of participating businesses and additional details on how to sign up will be available via the Nantucket Chamber of Commerce website closer to the time of the event.

Hear from the Great Point Properties Team

We asked our Great Point Properties team to share the Nantucket shops they love most, here are a few of their favorite places to browse this fall.

Ally Ulmer, Marketing Manager: “One of my favorite fall go-to shops on Nantucket is Core. Not only are they our neighbors at Great Point Properties, but they also have some of the best fall activewear on the island. I especially love that you can find wellness accessories there, too, from weighted bangles to yoga mats and other pieces that can be hard to find elsewhere.”

Stuart Reid, Sales & Rental Agent: “I recommend checking The Tennis Loft at the Jetties, owned and run by Tina, who is a great asset to Nantucket’s tennis and pickleball community.”

Tracy Cullinane, Sales & Rental Broker: “My favorite local shopping find is especially close to home. My boyfriend, Patrick, opened a summer pop-up for his custom surfboard brand, Banh Pho Surfboards, and clothing brand, Coterie De Surfeurs Pelagiques. The shop offered hats, tees, hoodies, and handmade canvas totes, with everything branded right in the shop using a shirt press or sewn patches. While the pop-up was only open for the summer, the collection is still available online.”

Nicole Bousquet, Rental & Sales Broker: “I also love our very own Katie Seholm’s shop, Patina, now located on India Street. It’s a wonderful local spot to browse, and I always love supporting one of our own Great Point Properties team members.”

Lexy Sabelhaus, Real Estate Agent: “I love Stephanie’s. I recently needed accessories for an event and found the most perfect pink bag and matching shoes there, plus a great dress I wasn’t even planning to buy! Stephanie was so helpful, and the shop has everything from beautiful clothing to fun, one-of-a-kind pieces, including their bird candlesticks.”

Madison Gilbert, Sales & Rental Agent: “For Now! is a great blend of clothing and home décor. They have affordable price points and an ever-changing collection throughout the season, so there’s always something new to discover. It really has something for everyone.”

Alexa Coleman, Sales & Rental Agent: “My favorite store in town is Milly and Grace. This locally owned business is operated by the most lovely family who will greet you with the most genuine smiles every time you walk through the door. Their curated collection of dresses, sweaters, housewares and jewelry changes every season and is always on trend. I can always find a great outfit for all sorts of occasions or a really lovely gift. Their sales are also really great. The ivy covered storefront is a must visit when shopping downtown!”

Nantucket in the Fall

If you’ve never experienced Nantucket in October, this is a perfect excuse to make a trip. The island is quieter, the weather is crisp and beautiful, and downtown is still full of local shops, restaurants, and businesses to explore.

And if you’ve visited Nantucket in the fall before, you already know there’s something special about the island this time of year. With the summer crowds gone, October offers a chance to experience some of your favorite places at a more relaxed pace while discovering something new along the way.

Why Not Make a Fall Getaway Out of It?

If you’re coming from off-island, why not stay for the weekend? A few extra days gives you plenty of time to shop downtown, enjoy a leisurely meal, take a walk along the beach, or simply experience the island at a slower pace.

Great Point Properties has a variety of Nantucket vacation rentals available this fall, giving you the perfect excuse to turn a shopping weekend into a full island getaway. Browse our fall vacation rentals to find a home for your stay.