The Best Things to do on Nantucket in October
Many people say October is the best month on Nantucket. Early October is still wedding season on the island as well, and there are plenty of fun activities for your guests to enjoy!
Eat your way through Restaurant Week
This year’s Nantucket Restaurant Week is September 28 through October 4, 2026.
Many of the island’s restaurants offer special seasonal menus, and the event has expanded well beyond restaurants to include private chefs, caterers, and food trucks. Two highlights bookend the week: a "Savor the Island" cooking demonstration on October 1 at Café 22, and a Food Truck Festival at Children's Beach on October 4.
Some of my favorite restaurants on-island (restaurant week or not) include Nautilus, Brotherhood of Thieves, Cru, Via Mare and Sistership. It's really hard to go wrong here though!
A helpful tip for both September and October visitors is to check social media or call ahead on Thursday and Friday nights especially! September and October are wedding season on Nantucket so many locations may be closed for wedding weekend related events!
The Bartlett’s Tomatoes & Burrata at Nautilus
It’s dark and moody in there.. and oh so delicious!
Catch the island's fall festivals and events
Here's what's on the calendar:
ACKtoberfest at Cisco Brewers (October 3rd & 4th) — the brewery's German-style beer festival, typically held the first weekend of the month with live music, a keg-holding competition, pretzel specials, and the release of their Acktoberfest Festbier lager. Check Cisco Brewers' events page closer to your trip for the confirmed date.
Wet Paint Weekend (October 9th –11th ) — local and visiting artists paint the island's landscapes en plein air, with finished works often for sale.
Cobblestones & Commerce (October 9th–12th) — a Chamber of Commerce celebration spotlighting downtown shops and businesses as the season winds down.
How the Event Works
Get a Card: Pick up a shopping bingo card at any participating business or the Nantucket Island Chamber of Commerce office at Zero Main Street.
Shop and Stamp: Visit participating stores and spend at least $10 to receive a stamp on your card.
Win Prizes: Each stamp counts as one entry for a chance to win prizes. More shops mean more chances.
Turn It In: Drop off your completed bingo card at the Chamber office on the second floor of Zero Main Street when you finish shopping.
Nantucket Half Marathon (October 11) — now in its 15th year, this run draws both serious racers and locals cheering from front porches.
Levitate Flannel Jam at Cisco Brewers (October 12) — an all day concert and celebration of Fall at the iconic Cisco Brewers. This festival sells out every year so buy your tickets while you still can!
Nantucket Conservation Foundation Fall Festival & Batacular Bike Race (October 25) — held at the Milestone Cranberry Bog, this is Nantucket's answer to a cranberry harvest festival.
Halloween Main Street Parade (October 31) — one of those Nantucket events when the island really turns into a Hallmark movie. Main Street is closed to vehicle traffic so kids can parade in their costumes and collect candy from the local stores! We have not yet decided what our family costume will be… any ideas?
The Sustainable Nantucket Farmers & Artisans Market continues every Saturday through October 31st. It features locally grown crops and island crafters.
Flannel Jam at Cisco Brewers
Indoor Events
A visit to the Whaling Museum or the island's other historic properties can be the perfect outing for a cooler day. Check website for tour times. Other indoor activities include the Shipwreck and Lifesaving Museum, an afternoon movie at The Dreamland,
or… get outdoors!
Fall is prime oyster and scallop season on Nantucket, and this is reflected everywhere from raw bars to the Scallopers Ball itself. So grab your scallop rake and permit and go dig up some fresh ones!
The Nantucket Conservation Foundation does an amazing job maintaining and creating new trails throughout the island. There are so many to explore! They even have an app!
Through the woods and to the ocean we go!
A few more practical notes
October weather on Nantucket is genuinely variable — pack layers, a windproof jacket, and don't assume beach weather, even though warm, sunny days absolutely happen. Many restaurants and shops shift to reduced or weekend-only hours after Columbus Day, so if a specific spot is on your must-visit list, call ahead or check hours before you go. Ferry schedules also thin out as the month progresses, so book your Steamship Authority or Hy-Line crossing in advance, especially around Restaurant Week, the Half Marathon, and Flannel Jam weekend, when the island fills up more than a typical fall weekend.
October won't give you a crowded beach day, but it will give you a quieter, more relaxed version of Nantucket .
