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18 Ways to Celebrate Fall in Nantucket


Events & Traditions

Gaelan Truyman
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With Nantucket being so seasonal, many people think the island shuts down after August, but au contraire! The island’s outdoor activities continue week after week and we typically enjoy fantastic weather in September and early October. Most restaurants and shops stay open until Columbus Day, with many staying open longer. The beaches remain fabulous as the water and weather temperature stay warm and the crowds thin out.

Accommodations are much easier to come by and if you’re considering a last-minute trip, call us today to find out which of our properties are available this fall in Nantucket.

Here are Fisher Real Estate’s top 18 fall activities to look forward on Nantucket!

Nantucket Harvest Fair

The Nantucket Island Fair and Cranberry Festival has merged to create a new event in 2022 called the Nantucket Harvest Fair. Head out to the Milestone Cranberry Bogs at 220 Milestone Road on October 1st and 2nd to experience all the fall magic Nantucket has to offer.


Agent Danno Lynch loves to golf in the fall. He says, “the light in the fall really makes for an extremely aesthetic golfing experience. The golf courses on island really pop and add incredible shadows.” Visit the public (and exceptional!) Miacomet Golf Club which is open year-round; they only close for inclement weather like frost or snow. Call them at 508-325-0333. Siasconset Golf Club, also known as “Skinner’s,” stays open through Columbus Day and weather permitting may stay open until the end of October. Call Skinner’s at 508-257-6596 for current hours (tee times are first come, first serve).


It’s no secret we LOVE to fish and we look forward to these tournaments all year. For an up to date fishing report, read the Bill Fisher Fishing Report which is updated regularly in-season.

Whaling Museum & Historic Sites

The Whaling Museum is open Monday-Saturday (closed Sundays) from 10am-5pm from September 12–October 10, and 10am–4pm October 11–December 31. Their historic sites vary so be sure to check out their website for up to date information. You can explore the exterior of the properties if they are not open to the public. Nantucket Historical Association historic properties include the Oldest House, Old Gaol, Greater Light, Fire Hose Cart House. The last historic property, the Old Mill, is celebrating its 125th anniversary since the organization purchased the Old Mill in 1897. Join them for a free event on October 22nd, 2022.


Sankaty Lighthouse and Great Point Lighthouse are incredibly beautiful in the fall, both the final destinations and the journey to get there. With golden foliage and light, it may be the best time to visit our historic beacons. Brant Point, of course, is beautiful year-round. Most importantly, don’t forget your camera!


The “family” scalloping season begins on October 1st, 2021 and runs until March 31st, 2022. Recreational scallopers can take scallops Wednesday through Sunday. Get your permit at the Harbormaster’s office at 34 Washington Street. Ready to get your feet wet? Read our informative blog post on the Fall Scalloping Season in Nantucket. Fisher Tip: Nantucket Bay scallops come in all sizes but keep in mind that in order to keep the scallops you “catch” they must have a well-defined raised annual growth line on the shell.


Popular restaurants that may have been a challenge to get into this summer are now easier to enjoy. We will have to wait and see if we will be treated to Fall Restaurant Week. Most restaurants that participate in Restaurant Week on Nantucket offer a three-course prix fixe menu, but some offer options from their entire menu.

Cisco Brewers 

The summer crowd may clear out but the food trucks and charming bartenders remain all fall. We especially love fall at the Brewery when the attire changes from board shorts to flannels and the drink specials change from frozen sangria to hot Cisco Cider and Pumple Drumkin. The Levitate Flannel Jam is a fun Columbus Day event held on Monday, get your tickets here before they sell out.



If you have had your eye on something in one of Nantucket’s stores this summer, the fall is a great time to go shopping. Take advantage of deep discounts everywhere from the t-shirt and souvenir shops to designer boutiques.

Head into town from October 7-9 to shop fall deals during the Chamber of Commerce event, Cobblestones and Cranberries. Consider this the precursor event for shoppingStroll Festival weekend.


Local surfers like Sales & Rental Agent Danno Lynch love surfing in the fall. He says, “it’s great because the water is still warm, the crowds have thinned out and the hurricane season brings in large, clean waves. It’s pretty easy to find empty peaks and firing waves all to yourself!”

Sunsets During Fall in Nantucket

The sunsets that fall bring are second to none. But where to watch? It’s no question that Madaket is one of our favorite Nantucket neighborhoods for many of us at Fisher Real Estate.

Pumpkin Carving  

Because one of the best activities to do during fall in Nantucket is pumpkin carving, head over to Bartlett’s Farm! They can also provide you with the carving and painting tools, just purchase a pumpkin from the garden center. While you’re at it, you can pick up some decorative pumpkins for your doorstep!


There is nothing better than enjoying a bike ride around the island on a crisp fall day. Without the summer heat, it is much easier to take a leisurely ride out to ’Sconset, Madaket or Surfside on one of the island’s accessible bike paths. Find bicycle rentals on Broad Street, North Beach Street, Surfside Road and Old South Road.

Halloween on Main Street 

Following up on the heels of the Daffodil parade in the spring and July 4th festivities, the Nantucket Halloween parade on Main Street is a beloved tradition.  Islanders normally congregate for the parade that starts at 4:30pm on October 31st. Arrive to town early for easy parking and see all your friends trick-or-treating at the shops on Main Street- if you can recognize them! Prizes go out to the best dressed at the top of Main Street at 5:00pm.

Nantucket Half Marathon 

nantucket half marathon

The Nantucket Half Marathon looks forward to putting up the finish line again on Columbus Day Weekend, Sunday, October 9th, 2022. This run is one of the most scenic half marathon courses on the East Coast! Visit their website here, or read Liza’s blog on running for some great info on running on Nantucket.

Nantucket Shorts Festival 

nantucket shorts festival

We love the Shorts Festival at The Nantucket Dreamland and shows films ranging in length from 2 minutes to 10 minutes, all made by local amateur and professional filmmakers. This year the Nantucket Shorts Festival will be held on Sunday, October 9th, 2022.

Third Annual Pitch Competition

Join Nantucket Island Chamber of Commerce and the Nantucket Island Center for Entrepreneurship (N.I.C.E.) for the Third Annual Pitch Competition, Saturday, October 8th, 7:30pm – 9:00pm at the Dreamland Theatre. 

The Fisher Real Estate team treasures the fall season on the island and believes it is one of the most wonderful times of year to visit Nantucket.  We hope to see you this season!

Link to Ferry Schedules and Late Fall Ferry Schedules


Written By

Gaelan Truyman

Gaelan is originally from Newton, MA and a graduate of UMass Amherst with a degree in Art History.