Fall in Love with this Tiny Island: What to Do and Where to Stay for the Perfect Autumn Adventure

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Exterior of 76 Main Ink Press Hotel in Nantucket, a luxury boutique hotel
This former sea captain’s home has been restored into a luxury boutique hotel. Photo credit: Cathy Bennett Kopf

“Everyone should have their own Nantucket.” The Mitchell’s Book Corner clerk shared this quote as she handed over my purchase.

I knew exactly what she meant.

Nantucket’s identity shifts dramatically with the seasons, so choosing when to visit depends on the vibe you’re looking for.

Want to be alone? You’ll have the island all to yourself in winter when most of the shops, restaurants and hotels close. Spring is exciting as everything reopens and the annual Daffodil Festival kicks off the new season. If you’re looking for the Nantucket featured in The Perfect Couple on Netflix, visit during summer, the prime tourist time, when the tiny island’s population swells to more than 100,000.

Me? I fell for fall.

Although the blue hydrangeas have turned to blush and the island rolls up the sidewalks at 9 pm, there are plenty of fun things to do in the autumn in Nantucket. I’ve provided some of my favorites plus tips for navigating the closures associated with the season. I’ve also included a review of the 76 Main Ink Press Hotel, a delightful boutique hotel, ideally located at the north end of Main Street in a residential neighborhood, steps from downtown shops, restaurants and the ferry.

The secret to the perfect Nantucket getaway? Make it your own.

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Summer vs. Fall in Nantucket

Families flock to Nantucket in summer for endless fun on the island’s sun-soaked Atlantic beaches. Downtown’s cobblestone streets are busy and buzzy, filled by day with well-heeled shoppers weaving their way through fab boutiques. Beautiful party people fill the bars at night and music and laughter provide the evening soundtrack. Nantucket is a high-end beach destination, not a shore town honky tonk. You’ll want to dress to impress.

After Labor Day, Nantucket takes a minute to catch its breath before settling in for a long winter’s nap. Restaurants, shops and hotels begin to shutter their doors for the season. The young and fabulous have migrated to Florida’s Palm Beaches and the locals have time to share the many reasons they love this rugged island 30 miles from Cape Cod.

My husband and I felt like we had the island all to ourselves. It was the sentiment shared by the other couples we met while having breakfast in the sun-filled kitchen at the 76 Main Ink Press Hotel. Most were New Englanders celebrating wedding anniversaries. Several, like us, were visiting Nantucket for the first time. The vibe on the island was laid back. The weather, except for one rainy day, was ideal for exploring.

Here’s where we went, what we did and some of the things we can’t wait to try on our next visit.

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The recovered skeleton of a sperm whale hangs in the Whaling Museum’s Gosnell Hall. Photo credit: Cathy Bennett Kopf

Tour the Whaling Museum

On that one rainy day, we headed inside the Whaling Museum and spent two hours exploring the fascinating exhibits focused on Nantucket’s history and maritime economy.

The museum’s highlight is the sperm whale skeleton installed in the museum’s Gosnell Hall. A distressed whale was spotted off ‘Sconset Beach in December 1997. The locals watched the whale for days, hoping it would recover and head out to sea, but it beached itself and perished on New Year’s Day. Volunteers using traditional whaling tools and modern equipment, under the supervision of federal and state authorities, stripped the whale and the Nantucket Historical Society was designated the caretaker of the impressive skeleton.

Docents give lively talks throughout the day describing the rise and fall of the whaling industry, accompanied by slides and short films. Be sure to head to the museum’s observation deck for a bird’s eye view of the Nantucket harbor.

Whaling Museum admission includes an audio tour and admission to Hadwen House, a Greek Revival mansion with an impressive display of traditional Nantucket lightship baskets.

SheBuysTravel Tip: The museum is the most popular attraction in Nantucket and gets crowded, even in the fall. I suggest arriving soon after opening to avoid the crowds.

Interior of the Great Hall in the Atheneum, Nantucket's public library and community hub.
The library staff served cider, popcorn and candy during the screening of the scary silent flick, Nosferatu. Photo credit: Cathy Bennett Kopf

Check Out the Library

The island’s community hub is its public library, the Nantucket Atheneum. The original building was destroyed during the Great Fire of 1846 but was rebuilt within six months. The Atheneum offers a wide range of youth and adult programming and events in addition to traditional library services.

Check the library calendar when visiting. Parents traveling with kids can access story hours for littles and teen trivia sessions. During my stay, the library kicked off Halloween with a free double-feature “Chills and Thrills” screening of classic horror flicks in the library’s Great Hall.

Nantucket Restaurant Week

Nantucket’s tourist migration follows a distinct cycle. Hotels and shops reopen in April, following a winter hibernation that begins after the Christmas Stroll. The summer months are crazy busy. Then there’s a lovely lull from Labor Day through Columbus Day.

A fall highlight is the annual Restaurant Week sponsored by the Chamber of Commerce. Discounted prix fixe menus are available at many of the island’s top restaurants during early October. The dates flex; so check the Chamber’s website for information including participating restaurants.

I arrived on the final day of Restaurant Week so I missed the deals, but I still managed to eat my way from jeans to stretch pants over the course of three days. Here are some of the highlights:

Brotherhood of Thieves

Known as The Brotherhood, this 1840s whaling bar is a lively hangout with good food. It’s popular, even off-season, so reservations are recommended.

Exterior of The Club Car in Nantucket.
Enjoy live music in The Club Car. Photo credit: Cathy Bennett Kopf

The Club Car

A solid downtown lunch spot, the restaurant’s Pullman car from the long-defunct Nantucket railroad is an evening piano bar.

Town

Located behind the Atheneum, Town is ideal for an intimate dinner for two. The “American Eclectic” menu, featuring sushi, a Portuguese seafood stew and Burgundy braised short ribs, is also available at Town’s sister establishment Queequeg’s.

The Downyflake donuts, chowder and sandwich in Nantucket.
Chowder, 1/2 a sammie and donuts. Here’s hoping The Downyflake finds a new home. Photo credit: Cathy Bennett Kopf

The Downyflake

A Nantucket institution, The Downyflake is where the locals go for breakfast and lunch. Sadly, the restaurant’s building is slated for demolition and its fate is unclear as of this writing.

Dune

I loved the Rhode Island calamari at Dune. Instead of the usual marinara sauce, the crispy squid rings were accompanied by a spicy green jalapeno sauce. The current chef/owner has announced his retirement, so expect changes at this popular restaurant.

Lobster quesadilla at Charlie Noble in Nantucket
Lobster quesadilla at Charlie Noble with sweet corn and a jalapeno relish. Photo credit: Cathy Bennett Kopf

The Charlie Noble

One of Nantucket’s few year-round restaurants, Charlie Noble is open for lunch and dinner, with an all-day raw bar and harborside outdoor patio. Even if you’re not in the mood for a full meal, I highly recommend a platter of sparkling Nantucket oysters and a gin & tonic.

SheBuysTravel Tip: Almost all of Nantucket’s restaurants close in the fall, based on the weather, staff availability and tourist traffic. So the dining experiences that summer visitors rave about might not be available. But that doesn’t mean you can’t get a great meal; you just need to be flexible. And be prepared to eat early. The restaurants I visited had crowds at 6:30 and emptied out by 8:30.

Exterior of Bartlett's Farm market store in Nantucket.
Bartlett’s Farm market store is a great place to stock up on provisions if you’re renting a house for your stay. Photo credit: Cathy Bennett Kopf

Pack a Picnic at Bartlett’s Farm

The Bartlett family can trace its Nantucket roots back to 1795. Through the centuries, they’ve raised dairy cows, cattle and sheep and currently operate a 200-acre farm on Nantucket’s south shore. It’s one of the island’s most popular attractions, offering farm tours and pick-your-own flowers in season.

The market and garden center are open year-round and the farm kitchen offers breakfast, lunch and dinner to-go menus.

A variety of items featuring hydrangea at For Now boutique in Nantucket.
If Nantucket had an official shrub, it would be the hydrangea. Photo credit: Cathy Bennett Kopf

Shop the Fall Sales

The boutiques clustered along downtown Nantucket’s cobblestone streets offer a dreamy selection of clothing, home decor and jewelry. Although you’ll find preppy national retailers like Lilly Pulitzer and Vineyard Vines, most of the shops are independently owned and uniquely curated. And the prices are sky-high.

But the shops shut down in the fall, so you’ll find plenty of sale racks and bins with items substantially discounted. It’s a great opportunity to snag a showstopping dress for a wedding you might have next summer. Here are some of the “only in Nantucket” stores you won’t want to miss:

Murray’s offers a variety of items in its iconic Nantucket Red. Photo credit: Cathy Bennett Kopf

Murray’s Toggery

The preppy uniform, suitable for cocktail parties, funerals and every event in between, consists of a navy blazer, button-down Oxford shirt and salmon pink pants. The color, known as Nantucket Red, was inspired by northern French boat sails. You’ll find the originals at Murray’s, which launched them in 1960. The store began as R.H. Macy’s in 1843. He later opened a pretty famous department store in NYC.

Elin Hilderbrand with a fan at a book signing in Nantucket.
This author meets THE author. Photo credit: Cathy Bennett Kopf

Mitchell’s Book Corner

I’m a huge fan of independent bookstores, the smaller the better. They generally reflect the owner’s personality and, especially in tourist destinations, have a nice selection of local authors represented.

I wasn’t familiar with Nantucket author Elin Hilderbrand’s romantic novels until the hype for the Netflix series The Perfect Couple hit my feeds. I read the book and watched the series simultaneously. No spoiler alert – they’re quite different – and, while I liked the series, I enjoyed the book much more. Hilderbrand made weekly book signing appearances at Mitchell’s in 2024. And, although she’s announced to fans that she’s discontinuing her Nantucket series, I expect she’ll continue the book signings in the coming years.

Exterior of Aunt Leah's fudge in Nantucket.
My only Nantucket regret? Not buying more fudge. Photo credit: Cathy Bennett Kopf

Aunt Leah’s Fudge

Located near the Hy-Line ferry dock on Straight Wharf, Aunt Leah’s is a must-stop for what’s advertised as “The World’s Best Fudge.” I’ve not sampled enough to confirm this, but the fudge is pretty darn good. Seasonal flavors feature Nantucket cranberries.

Hang Ten raw bar, a vendor at Cisco Brewers in Nantucket.
Oysters and beer? It’s a perfect couple at Cisco Brewers. Photo credit: Cathy Bennett Kopf

Sip a Beer at Cisco Brewers

Don’t skip a trip to Cisco Brewers. The outdoor complex is a fun spot to listen to music, sip a beer or two and slurp some oysters. You’ll want to check the website for fall operating hours, available food trucks and the free shuttle schedule before heading out to their location on Bartlett Farm Road.

I visited on an October Tuesday afternoon and there was a surprisingly good crowd – a nice mix of families, dogs, couples and friend groups gathering around picnic tables in the autumn sunshine. I’ll be seeking out Shark Tracker, Cisco’s light lager, at my local beverage center when I get home. It’s a very drinkable brew and proceeds from sales support white shark research.

Sankaty Head Lighthouse in 'Sconset on Nantucket.
A stop at Sankaty Lighthouse is included on Gail’s Tours. Photo credit: Cathy Bennett Kopf

Explore the Island

Nantucket is small. It’s 14 miles long, 3 1/2 miles wide and flat. If you’re the biking sort, you can rent bikes from one of the local agencies by the wharf and head off on a cycling adventure. Young’s Bicycle Shop has a printed map showing the island’s dedicated bike paths.

If you prefer to wander on foot, I suggest stopping by the Visitor Information Center on Federal Street. The friendly staff will assist with providing trail information. Lina Gillies was on duty when I stopped in. She told me her favorite Nantucket fall thing was lighting her first fire. Then she gave me directions to the Hays Overlook, an accessible, .25-mile paved trail with an awesome creek view.

Since hubby has a scheduled knee replacement, we opted for an outing with Gail’s Tours. Gail’s family has lived on Nantucket for seven generations; her forebears include some of Nantucket’s most famous names including the Gardners and Folgers (yes, the coffee Folgers). Our 2-hour tour on a 14-person van departed from the Visitor’s Center and drove past island landmarks including The Old Mill and The Oldest House. We stopped in ‘Sconset at the Sankaty Head Lighthouse for photos. Gail was very responsive to questions and dropped us off outside of downtown at The Downyflake at the end of the tour.

Next time, I want to get out on the water to see Nantucket’s millionaire mansions. Sport fishing expeditions, sunset cocktail sails and family ice cream cruises are a few of the available options offered by Nantucket by Water.

Rear facade of The Wauwinet, Nantucket's historic luxury hotel with green chaise lounges positioned to face the ocean.
The Wauwinet is a Nantucket institution. Photo credit: Cathy Bennett Kopf

Have a Cocktail at Topper’s

Topper’s is the AAA 5-star restaurant at The Wauwinet, the only Relais & Châteaux hotel on the island. The Wauwinet has welcomed guests in grand style to the classic, cedar shake property on the northeast tip of Nantucket since 1875.

If the rooms are above your price point, I suggest you head out for an afternoon cocktail at Topper’s bar. You can sip your drink and soak up the ocean views on the outside patio. If the weather’s not great, the indoor bar is intimate. We cozied up to the bar and chitchatted with a father and daughter who return annually for lunch and a cocktail at The Wauwinet to celebrate her birthday.

SheBuysTravel Tip: We were going to request an Uber to return to town, but the pair told us that we could trek back on the hotel’s complimentary guest shuttle which runs daily from the hotel on the 1/2 hour. Downtown pickup/dropoff is at the Visitor Center.

Lounge at the 76 Main Ink Press Hotel in Nantucket.
Past and present Nantucket mastheads make a statement in the hotel’s lounge. Photo credit: Cathy Bennett Kopf

Where to Stay: 76 Main Ink Press Hotel

A central location is the key to a great Nantucket getaway. The 76 Main Ink Press Hotel, a 20-room converted sea captain’s home, sits on Main Street where the business district yields to residences. All of downtown’s restaurants, shops and attractions are steps from the hotel’s front steps. But the neighborhood has a “no noise after 9” policy, so evenings are quiet, perfect for a good night’s rest.

A recent renovation of the property puts the focus on Nantucket’s headlines and headliners. The hotel comes by its press heritage honestly. The owner, Bruce A. Percelay, is the founder and publisher of N magazine and The Nantucket Current. Public spaces are playfully decorated with press elements, including oversized typewriter keys and the names of past and present island newspapers.

76 Main Guest Rooms

Guest rooms in the main house come in a variety of configurations including standard and deluxe kings and queens. Meeting Nantucket’s strict historic preservation standards required some ingenious layouts, particularly when designing the bathrooms. If you don’t immediately see a toilet in its expected location, it’s probably in a separate converted closet. Open all the doors before calling the front desk.

Outdoor fire pit seating at Nantucket's 76 Main Ink Press Hotel.
FinishedThe Perfect Couple then napped in the cozy garden. Photo credit: Cathy Bennett Kopf

If you prefer a summer bungalow feel, opt for one of the hotel’s cottage rooms. They’re separated from the main house by a large outdoor garden area with tables, lounge chairs and a massive fire pit. All the cottage rooms have screen doors and some have private “backyard” spaces with fire pits and Adirondack chairs.

Cottage room at the 76 Main Ink Press Hotel.
Our roomy, shark-themed cottage room. Photo credit: Cathy Bennett Kopf

All the rooms offer a unique shoutout to someone or something with a Nantucket connection. My cottage room was devoted to sharks with a framed story from N magazine about the uptick in shark activity featured in a 2023 documentary “After the Bite” centered above the room’s coffee station. A surfboard with a bite removed hung above the chaise lounge. There’s an Elin Hilderbrand room with the author’s book covers and signature on the room’s beam. What’s consistent throughout is the coastal color scheme that leans into greens, blues and 76 Main’s interpretation of Nantucket red.

Buffet space at the 76 Main Ink Press Hotel.
Gather in the light-soaked Press Room for breakfast and happy hour. Photo credit: Cathy Bennett Kopf

Hotel Amenities

Rates include a continental breakfast. During my stay, yogurt parfaits, savory and sweet croissants and mini corn muffins were some of the items served buffet-style in the main house kitchen. In the afternoons, a mixer bar is set up for guests to host their own BYOB happy hour. I thought this was such a great idea. Chips, sodas and fresh-from-the-oven cookies are available too.

The hotel staff are happy to help you curate your own Nantucket experience. Don’t hesitate to ask for assistance with restaurant recommendations and reservations or to book charters and tours.

Cathy Bennett Kopf serves as the Daily Editor of SheBuysTravel, reporting to Editor-in-Chief Cindy Richards. She began travel writing after serving as the unofficial (and unpaid) vacation coordinator for hundreds of family and friend trips. She launched her blog, The Open Suitcase, in 2012 and joined the SBT (formerly TravelingMom) team in 2016. A lifelong resident of New York, Cathy currently resides in the scenic Hudson River Valley. She’s a member of the Society of American Travel Writers, the International Travel Writers Alliance and TravMedia.
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