The Best Things to Do on Nantucket in September 2026

What are your plans for September?

September might be the best-kept secret for things to do on Nantucket. The summer crowds thin out right after Labor Day (Monday, Sept 7), the water's still warm, and the island's event calendar shifts from beach-day energy to county-fair, harvest, and gallery-season energy. Here's every confirmed event on Nantucket this September, plus a couple that spill into early October. Here are The Best Things to Do on Nantucket in September 2026
What's happening on Nantucket in September 2026?

The month's anchor weekend is September 12–13, when the Nantucket Island Fair and the AAN Sidewalk Art Show land on the same Saturday. From there, the calendar fills in with a golf tournament for the hospital, a farm bike tour, a cross-island hike, rotating gallery shows, and — closing out the month — the return of Nantucket Restaurant Week.

Nantucket Island Fair — September 12–13
The island's classic county fair returns to Tom Nevers Field, 10 am–4 pm both days. Saturday is the bigger of the two: Ray's Barnyard (alpacas, goats, pigs, and more), Gertrude's Farm Stand, baking competitions for tar roof cake and cookies, a fairy house contest, sack races, a watermelon-eating contest, and a wattle balloon toss. Sunday trades some of the county-fair games for a dog show (registration 11 am, judging at noon) and a 1 pm flower-arranging workshop. Both days include Artisans Alley, livestock exhibits, a dunk tank, a scavenger hunt, and ticketed Kids Corner activities like tie-dye and pumpkin painting.
AAN Sidewalk Art Show — September 12
Same Saturday as the Island Fair, the Artists Association of Nantucket sets up its free outdoor Sidewalk Art Show in the Nantucket Atheneum Gardens downtown — an easy add-on if you're already on the island for the fair. It bookends a busy month for AAN's gallery, too: the 10x10 Open Exhibition runs September 3–22 (opening reception Sept 3 at 5 pm), followed by the People's Choice Exhibition from September 24 through October 6.
Sankaty Swing golf tournament — September 14
A fundraiser for Nantucket Cottage Hospital, the Sankaty Swing tees off at Sankaty Head Golf Club. It's a members-and-sponsors tournament rather than a drop-in event, so if you're interested in playing or sponsoring, go through Nantucket Cottage Hospital's events page directly for 2026 registration and pricing.
Sustainable Nantucket Farm & Field Bike Tour — September 15
A guided bike tour celebrating the island's working farms, run by Sustainable Nantucket. It starts at Moors End Farm (40 Polpis Road) and runs 9:30 am–1:30 pm — a nice way to see the agricultural side of Nantucket that most visitors never get to. Sustainable Nantucket also hosts a members' annual meeting on September 16 and a NantucketGrown farm-to-table dinner at Topper's Restaurant on September 23, 6–8 pm, if you want to eat your way through the island's harvest instead of biking it.
Cross-Island Hike — September 19
The Nantucket Land Bank's Cross-Island Hike is a free, guided walk from Tom Nevers Fairground beach to Settler's Landing on Madaket Harbor, starting at 8 am on Saturday, September 19. Because parking is limited at the start, the Land Bank runs shuttle transportation — you'll need to register online in advance — but there's no shuttle back at the end, so plan your own ride home (rideshare, taxi, or a friend with a car).
Nantucket Restaurant Week — September 28–October 4
The fall edition of Nantucket Restaurant Week wraps up the month and spills into early October, with special prix-fixe and featured menus at restaurants across the island. It builds to a Grand Tasting on October 1 and closes with a Family Food Truck Festival on October 4 — worth planning a trip around if you're the type who plans vacations by menu.
The Sustainable Nantucket Farmers & Artisans Market keeps going too
If you're on-island any Saturday this month, the Farmers & Artisans Market runs weekly through October 31 — local produce, baked goods, and artisan crafts, and a reliable way to spend a Saturday morning even on a week with nothing else on the calendar.
Wind down after a day of island events
Whichever September event brought you out — the fair, the hike, the bike tour, or just Restaurant Week hopping — swing by ACK Natural on your way back. We're at 19 Spearhead Drive, five minutes from downtown, open daily 10 AM–7 PM (10 AM–8 PM Fridays and Saturdays). Our flower page and edibles page cover the full menu — everything grown and made right here on Nantucket, at the island's only on-site cultivation and licensed medical cannabis facility.
Dont forget about the live music on Nantucket, you can check out our Live Music Blogsweekly blogs

Browse the menu and order ahead for fast pickup. Must be 21+ with a valid ID.