Planning a vacation in Nantucket this fall? Here are the 9 best things to do on Nantucket Island!

The idyllic island of Nantucket has become a top summer vacation and second home destination in New England. Its endless sandy beaches, remarkably preserved historic sites, blooming hydrangeas and roses, and charming cobblestone streets alongside the untouched natural habitat attract millions of visitors every year.

During the peak of the summer season, the number of people residing on this island can swell up from 10,000 to 50,000 people.

But, for some people, the best-kept secret of Nantucket, MA, is visiting it in the fall.

This is the time when the crowds have left. At the same time, the weather is still wonderful, and most restaurants, museums, shops, and venues are still open and fully functioning so there are plenty of things to do in Nantucket in the fall.

One of the best parts about choosing the fall for your trip to Nantucket is that you will get a much wider choice of available short-term rental lodgings, or hotels, at much more affordable prices.

Plus, you won’t have to wait for days and weeks to get a table reservation at some of the best restaurants on the island.

If you have already unraveled this well-kept secret and will be traveling to Nantucket this fall, here are some tips for the best things to do there in the autumn months.


best things to do in nantucket visit lighthouse
Best things to do in Nantucket this fall: visit the historic lighthouses

1. Explore the historic sites

Thanks to the never-ending efforts of the local authorities, non-governmental organizations, and the tight-knit community itself, Nantucket has some of the best preserved colonial buildings, cobblestone streets, lighthouses, and other historic sites in the country.

You can sign up for the Downtown Walking Tour or the Historic Homes and Architecture Tour organized by the Nantucket Historical Association to learn some fascinating facts about the island’s history. You will be able to admire over 800 of the finest surviving and restored pre-civil war buildings in New England.

The entire island of Nantucket was designated as a Historic District in the National Register of Historic Places back in 1966.

While there, you can see the oldest working smock mill in the USA – the Old Mill. Other historical sites to see are the Old Gaol, Oldest House, the Fire Hose Cart House, and others while taking one of the self-guided walking tours during the fall.

Of course, don’t forget to visit the three historic lighthouses on the island, including Sankaty Head Light, Great Point Light, and Brant Point lighthouse. They are even more beautiful during the fall, so don’t forget your camera.


top things to do in nantucket harvest fair
Top things to do in Nantucket in autumn: go to the Nantucket Harvest Fair

2. Attend the Nantucket Harvest Fair

In 2022, the two leading fall events in Nantucket – the Cranberry Harvest Festival and the Nantucket Island Fair will be combined into one Nantucket Harvest Fair.

This family-friendly event will take place on October 1st and 2nd and, as usual, will be situated at the Milestone Cranberry Bogs. It will include events and festivities, including live music, contests, shows, and others. Some of the leading events include the giant pumpkin contest, the Dahlia show, the dog show, and more.

The local cranberry farming has a history of over 200 years. The peak of the cranberry harvesting season is from late September up until the end of October.

Even if you can’t make it to the fair, you can still tour the cranberry bogs on the island and taste some fantastic cranberry treats and drinks.


popular things to do in nantucket scalloping massachusetts
Popular things to do in Nantucket in fall: go scalloping in Massachusetts

3. Go scalloping

If you are going to Nantucket Massachusetts after the summer season is over, you will get the unique opportunity to do some recreational scalloping.

The official family scalloping season on the island starts on October 1st and continues until the end of March.

You can enjoy recreational scalloping every week from Wednesday to Sunday. You will need a license and shell fishing button issued at the Nantucket Public Safety Building.

You can get the gear and wetsuit or waders you need for scalloping from the local marine shops.

Some of the leading locations for scalloping on the island include Monomoy and Madaket and other harbors of the Little Grey Lady of the Sea.


best things to do in nantucket golf vacation
Best things to do in Nantucket in autumn: plan a golf vacation on Nantucket Island

4. Go golfing in Nantucket this fall

There are two public and two private golf courses on the island. All are near the water and offer stunning ocean views. The link-style courses located along the coasts of Nantucket are reminiscent of Scotland, where such golf courses were first established.

Due to their unique seaside coastal views, sandy soils, beachy grass, and unpredictable breeze, the four golf courses are among the top preferred by many avid golfers.

The 18-hole public Miacomet Golf Course is open all year round. Just make sure that you book your tee time ahead of time. Luckily, this can easily be done online before you even set foot on the island.


cycling in nantucket in fall
Must-try things to do in Nantucket Massachusetts: go cycling around the island

5. Bike around Nantucket Island

Nantucket MA is a small-sized island with an extensive network of bike lanes. So one of the best ways to get around and enjoy the views and atmosphere there is via bike.

You can bring along your own bike via the traditional Steamship Authority ferry, or even better – rent one from a local rental.

Some homeowners and rental companies have included free bicycles as part of the amenities for their guests in the many short-term rental residences found around the island.


best things to do on nantucket island hike
Best things to do in Nantucket this fall: go on a beach hike on Nantucket Island

6. Try out some of the stunning hiking trails

Thanks to the dedication of the people of the island, nearly 50% of the land of Nantucket is protected. Many hiking trails on the island are suitable even for beginners as they are quite short and low impact, so there’s no wonder hiking is one of the best things to do in Nantucket all year round.

Some of the best ones to try out are the Tupancy Links or Sanford Farm trails. Each will take you to the coast, where you can enjoy the stunning ocean views.

You can also hike up to Altar Rock, the highest point on Nantucket.

There are guided maps available via the ACK Trails and the Nantucket Conservation Foundation app for all of the multiple trails in Nantucket.

For those of you looking for a challenge, you can sign up for the Third Annual Cross-Island Hike, which will take place on September 24th.


halloween parade nantucket in autumn
Unique things to do in Nantucket in autumn: join the Halloween Parade

7. Have fun on Main Street on Halloween

The Halloween Parade starts at 4 pm on October 31st and will pass through Main Street in Downtown Nantucket. Over 1,000 participants in fun costumes are expected to participate this year. So, if you happen to be in Nantucket on Halloween, make sure to join the fun festivities, and be ready to be spooked. There will be awards for the best dressed so that you can try out for a prize for the best Halloween costume.


top things to do in nantucket cisco brewery
Top things to do in Nantucket on vacation: visit Cisco Brewery

8. Spend an afternoon at Cisco Brewery

The outdoor local craft beer brewery is one of the top spots for the locals and visitors of the island. This is thanks to its wonderful beer garden, live music, numerous food trucks, and fun atmosphere.

But even if you decide to go to Nantucket after the summer season is over, you can still enjoy spending time at Cisco Brewers.

The brewery is next to the local winery and distillery, so there will be suitable drinks for every taste.

In the fall one of the most delicious things to do in Nantucket is to try the seasonal mulled wine and locally made Pumple Drumkin Pumpkin Ale and Cisco Cider are added to the menu.


best things to do in nantucket surfing
Best things to do in Nantucket this autumn: go surfing in Nantucket

9. Surf the waves

The local surfers on the island prefer the fall because of the thinned crowd and the best swells, beach break peaks, and surfing conditions.

In the autumn, when most of the tourists are gone, you can enjoy a less crowded and more fun surf scene as well as the sand bars, many of which are still open throughout October.


About the author

Mirela Letailleur The Travel Bunny

Mirela Letailleur is a Romanian travel blogger living in the South of France. She writes on The Travel Bunny travel blog about affordable travel in Europe. Creator of unique free travel guides and local travel expert. Problem solver. Wannabe coffee guru.

Read more about Mirela Letailleur

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