Photo of Brant Point Lighthouse by Tim Grafftmott courtesy of Massachusetts Travel & Tourism.
As Fall descends on Nantucket, New England foliage colors reveal themselves in shades of crimson and ochre, and East Coast vacationers slowly return to city life. Nestled off the coast of Massachusetts, this bucolic island is a haven of timeless beauty, and during the shoulder season, Nantucket’s peaceful appeal is amplified further.
From Sylvester Stallone to Drew Barrymore, Hollywood stars adore Nantucket’s privacy and beautiful beachside communities. But with society stars fully dispersed come Fall, Nantucket’s cobblestone streets, pristine beaches, and alluring trails become more secluded, allowing you to truly immerse yourself in the wonder of the island’s surroundings.
Whether you’re seeking a romantic autumnal escape or an off-season group getaway, Nantucket in the Fall promises an unforgettable experience. So, pack your favorite sweater, breathe in the salt-spray infused air, and prepare to fall in love with the island’s stunning natural landscapes, rich maritime history, and farm-to-fork cuisine.
Stay
Be it elegant heritage hotels or epic waterfront compounds (à la the A-list), you’re spoilt for choice with places to stay in Nantucket. For timeless harborside glamor, the iconic White Elephant has been a draw for Nantucket’s most discerning visitors for a century. Looking fresh after a multimillion-dollar revamp, the sprawling hotel now boasts a chic nautical vibe, with airy and bright rooms, a giant pool, and a serene spa. Savor a signature Lobster Bloody Mary at White Elephant’s legendary Brant Point Grill.
Perched on a blissfully quiet beach rather than in the main hubbub, The Wauwinet, White Elephant’s sister hotel, has been hosting guests since 1875 — 21st century stays are all about relaxation. Kick back in your homey, cottage-style room and gaze out over the garden across to shimmering Nantucket Bay. An adults-only hotel, The Wauwinet is Nantucket’s premier romantic bolt-hole.
For grandeur on a more intimate scale, Greydon House (a timbered, former sea captain’s residence) aligns heritage style with modern bohemian luxury. Each of the 20 rooms is uniquely appointed with eclectic antiques and characterful soft furnishings. Spend an evening lingering over fine, Venetian-inspired dishes at Via Mare, Greydon House’s much-hyped, wood-paneled restaurant.
Nantucket is teeming with luxurious estate rentals for exclusive private getaways. When Kourtney Kardashian and family vacationed on Nantucket, they chose a gorgeous Airbnb holiday hideaway over a hotel. For large family escapes, consider Luxury Cliff Rd Home in Brant Point. Namechecked in Vogue, this stunning seven-bedroom home is serenely appointed in cool whites, with a large pool for chill-out days.
The White Elephant Nantucket's Welcoming Front Porch Lounge. Courtesy of White Elephant Nantucket.
Dine
Nantucket’s vibrant culinary scene is all about the just-caught seafood and farm-to-table delights. The good news is that you’re just as likely to find sensational coastal cuisine whether you hit up a flash fine dining waterfront eatery or laid-back bistro.
Ask any local (or visiting high-roller) for their recommendation, and they’d likely point you in the direction of Straight Wharf. This Nantucket institution has been serving its clam bake and iced Nantucket oysters for over 50 years. On a balmy evening, snare a table on the harborside deck to watch boats bob while you savor the fruits of the Atlantic al fresco.
In downtown Nantucket, The Pearl’s stylish, Art Deco-esque environs create a wonderful backdrop for its incredible coastal Japanese-inspired dishes, whipped up with fabulous French techniques. Under new ownership, The Pearl has reimagined its 30-year legacy with innovative dishes such as salt and pepper wok-fried lobster with tatsoi and grilled lime.
You’ll feel right at home at Òran Mór Bistro; where prettily plated Italian-New England dishes are served in the cozy parlor of a smart historic house. Seat beside the fireplace and choose from black truffle bucanti or delightful fennel orecchiette pasta.
For Nantucket’s only AAA 5-diamond restaurant experience, seek out TOPPER'S at The Wauwinet. This is the island’s place to see and be seen — be it over a banquet brunch of oysters with Champagne mignonette or a roasted Gianonne chicken dinner — Topper’s offers irresistible ocean views as you rub shoulders with the Nantucket elite.
North Atlantic Lobster At Topper's. Courtesy of The Wauwinet.
Drink
At CRU Oyster Bar, you come for the oysters but stay for the fizz. This marina hotspot set amid rows of sleek yachts has a casual vibe but plenty of energy as the day fades to night. Arrive for sunset and settle in, perusing the gargantuan wine list. Flawlessly curated with drops from all over the world, you’ll find excellent Champagne vintages alongside Old and New World international wines. Order a dozen local oysters (or caviar if you’re inclined).
Since starting as an indie microbrewery, Cisco Brewers has grown into a brewpub behemoth, with outposts all over New England. Its Nantucket venue is still the original and best. A winery, distillery, and brewery all rolled into one, as well as producing world-class wines, beers, and spirits, the ever-popular Cisco Brewers hosts live music every day, public production tours, and pop-up street food vendors.
For a taste of the island’s most inventive cocktails, Nautilus presents masterful mixology. A buzzy bar-restaurant, Nautilus’ tapas-style small plates are best washed down with one of its imaginative (and strong) house libations. Take the zingy Nauti Dog; a lively vodka and Campari number mixed with ‘literally a whole grapefruit’. Or, for something spicy, try the Quick Tickle, with mezcal, itachi cucumber, and pickled jalapenos.
Overlooking Nantucket's Harbour At Straight Wharf. Courtesy of Straight Wharf Restaurant.
Do
Nantucket grew rich from its 19th-century whaling industry, and this has left an indelible maritime legacy that’s present everywhere you turn. Immerse yourself in the island’s whaling heritage at the Nantucket Whaling Museum. Learn about the island’s sea-faring past, view fascinating exhibits, and climb to the top of Tucker’s Roofwalk observation deck for panoramic harborside views.
Soak up the charm of Downtown Nantucket by meandering through its cobbled streets and historic buildings. Not only is it to-die-for pretty, but Downtown is the main shopping hub, awash with everything from art galleries and independent boutiques to artisanal stores. Pick up classic Nantucket Reds at Murray’s Toggery Shop, rare reads at Mitchell’s Book Corner, and exquisite home décor from Nantucket Looms.
Crowning the sandy dunes of Nantucket’s northernmost tip on the Coskata Coatue Wildlife Refuge, Great Point Lighthouse commands over the rolling Atlantic that laps below. If you’re up for the seven-mile walk to reach it, strap on your walking boots, but otherwise, a 4x4 is the best way to access New England’s most powerful light. Pick up a Jeep from a rental shop in Town, and, starting at the gatehouse, drive straight up to the Great Point lighthouse over the sandy route. Look for basking seals and skittering shorebirds along the magnificent coastal scape while you bump over dunes.
With waters still dip-worthy until early October, you’ll still be able to unfurl your towel on a Nantucket beach in Fall. The best? For never-ending golden sandy stretches, head to Madaket and Ladies in the south. Serene and less crowded, they’re perfect for long walks along the shoreline, picnics, and blissed-out sunsets. Or for gentle surf, make your way to north shore beaches like Jetties, Steps Beach, Dionis, and Brant Point.
Each year, the 1st of October heralds the arrival of several Nantucket food harvests. It’s the start of scalloping season, where Nantucket Bay scallops (the world’s most coveted, in fact) are harvested by hand and boat. If you fancy recreational scalloping for these plump, buttery, and sweet delicacies, off-islanders are invited to apply for a one-week permit and, armed with a snorkel, mask, and net, may dive to retrieve your shell-encased reward.
Just like whaling and lighthouses, the annual cranberry harvest is innately interwoven into Nantucket’s cultural landscape. For over 150 years, this zingy red fruit has been grown in the island’s wetlands, namely the Milestone Cranberry Bog — the world’s largest contiguous cranberry bog, measuring an extraordinary 234 acres. In Fall, Milestone Cranberry Bog hosts the annual Nantucket Harvest Fair where visitors can see how their tart fruits are harvested before joining in merry-making alongside live music, shows, and contests.
The Wauwinet Lawn at sunset. Courtesy of The Wauwinet.
Arrive-Depart
Nantucket Memorial Airport (ACK) offers direct flights from several major cities on the East Coast. Alternatively, you can fly into one of the nearby airports such as Boston Logan International Airport (BOS) or T.F. Green Airport in Providence (PVD), and then connect to a flight to Nantucket.
If a road trip is on your to-do list, determine your best route to reach one of the ferry ports that provide service to Nantucket. Depending on your starting location, you may need to drive to one of the ports in Massachusetts such as Hyannis or Woods Hole. Cruising time is just over two hours.