Downtown Nantucket Guide

Understanding Downtown Nantucket

Let me be straight with you about what makes downtown Nantucket different from any other charming coastal town: it's authentic. These aren't reproduction buildings or recreated streets designed to look historic. The architecture you see is the real thing—structures built in the 1700s and 1800s that have been continuously preserved, not rebuilt.

The town center is remarkably compact. You can walk from Steamboat Wharf (where the ferries arrive) to the far end of Main Street in about ten minutes. But don't let the small footprint fool you. Within this area, you'll find over 800 buildings dating from before the Civil War, making downtown Nantucket one of the most significant concentrations of pre-1850 architecture in America.

What most visitors don't realize is that this density of historic buildings isn't an accident—it's the result of a peculiar twist of fate. When the whaling industry collapsed in the 1850s, Nantucket couldn't afford to tear down and rebuild. Poverty preserved what prosperity would have destroyed. And now that preservation makes downtown Nantucket priceless.

Main Street and the Cobblestones

The cobblestones beneath your feet on Main Street aren't merely decorative—they're ballast stones from whaling ships, laid in the 1830s when Nantucket was the whaling capital of the world. Walk them slowly. Generations of sea captains' wives walked this same path, watching the harbor for ships that sometimes never returned.

Main Street stretches from the base of the Unitarian Church (whose golden-domed steeple has guided sailors home since 1809) down to the harbor. The upper section, known as Upper Main Street, features the grandest Greek Revival mansions—homes built by whaling merchants who wanted the world to see their success. The Three Bricks, built by Joseph Starbuck for his three sons between 1836-1838, are perhaps the most famous: three identical Georgian mansions that remain private residences today.

Lower Main Street transitions from residential grandeur to commercial charm. Here you'll find boutiques, galleries, and restaurants housed in buildings that once served as chandleries, sail lofts, and counting houses. The Pacific National Bank building, with its distinctive columns, dates to 1818 and still operates as a bank—one of the oldest banking locations in continuous operation in America.

Main Street Highlights

• The Three Bricks: 93-97 Main Street - Three identical 1830s mansions, architectural icons
• Hadwen House: 96 Main Street - Grand Greek Revival mansion, open for tours
• Pacific National Bank: 61 Main Street - Operating since 1818
• Mitchell's Book Corner: 54 Main Street - Independent bookstore since 1968
• First Congregational Church: 62 Centre Street - Climb the tower for panoramic views

The Wharves: Where History Meets the Harbor

Nantucket's wharves once bristled with the masts of whaling ships returning from three-year voyages to the Pacific. Today, they're home to fishing boats, yachts, and some of the island's best restaurants. But the bones of the old wharves remain, and walking them connects you directly to the island's seafaring past.

Straight Wharf

Straight Wharf is downtown's social center, especially in summer. The wharf extends into the harbor, lined with galleries, restaurants, and the Hy-Line ferry terminal. This is where you'll find some of Nantucket's most iconic dining experiences, with tables practically hanging over the water.

The secret here is timing. At sunset, the west-facing restaurants fill with golden light as the sun drops toward the harbor. Arrive early for drinks, secure a waterside table, and watch the fishing boats return with the day's catch—some of which will appear on your plate within hours.

Old South Wharf

Where Straight Wharf buzzes with energy, Old South Wharf offers a more intimate experience. The weathered gray shacks here house artist studios, boutiques, and quieter restaurants. Walk the wooden planks past boats bobbing in their slips, peek into galleries showing local artists, and discover why many repeat visitors consider this the most authentic corner of downtown.

My grandmother used to say that Old South Wharf is what all of Nantucket looked like before the tourists discovered it. She might have been romanticizing, but there's something undeniably genuine about this place—salt-worn, sun-bleached, and utterly Nantucket.

Commercial Wharf

Between Straight and Old South, Commercial Wharf houses more shops and the Nantucket Boat Basin marina. This is where you'll see the serious yachts—vessels that cost more than most houses. The people-watching is exceptional, and the wharf offers some of the best harbor photography opportunities on island.

Historic Sites Worth Your Time

This tradition of preservation dates back to the Nantucket Historical Association's founding in 1894. Today, the NHA operates over a dozen historic sites downtown, and a single pass grants access to all of them. Here's where to focus your time:

Whaling Museum

The building that now houses the Whaling Museum was once a candle factory—a reminder that whale oil literally illuminated the world before petroleum. The 46-foot sperm whale skeleton suspended in the main hall is breathtaking, but don't miss the rooftop walk with its panoramic views, the scrimshaw collection, or the Fresnel lens from Sankaty Head Lighthouse.

Location: 13 Broad Street
Hours: Open daily in season; check NHA website for current hours
Tip: The museum's introductory film provides essential context. Watch it first.

Oldest House (Jethro Coffin House)

Built in 1686, this is the oldest house on Nantucket and one of the oldest in New England. The horseshoe decoration on the chimney wasn't just ornamental—it was meant to ward off witches. The low doorframes and small rooms remind you just how different life was 340 years ago.

Location: 16 Sunset Hill Lane
Tip: It's a short walk from downtown. Combine with a stroll through the Old North Cemetery nearby.

Old Gaol

The 1805 jail held prisoners until 1933, making it one of the longest-operating jails in America. The logs prisoners carved while awaiting trial are still visible. It's a fascinating look at island justice—and injustice.

Location: 15R Vestal Street

Quaker Meeting House

The Quaker influence on Nantucket cannot be overstated—they dominated island society for generations and shaped everything from architecture to social values. This simple, powerful space reflects their belief that worship needs no ornament.

Location: 7 Fair Street

Shopping Highlights

Downtown Nantucket shopping is a different experience than mainland retail. Yes, you'll find national brands (Murray's Toggery, the home of Nantucket Reds, is technically a chain—of one). But the real treasures are the independent boutiques, many owned by island residents who curate their collections with genuine passion.

For Nantucket Classics

• Murray's Toggery Shop: The original source of Nantucket Red pants since 1945. The color fades to salmon pink with washing—a badge of authenticity.
• The Hub: Corner of Main and Federal. Newspapers, magazines, and a community gathering spot since 1929.
• Nantucket Bookworks: Broad Street. Local history, beach reads, and author events.

For Artisan Goods

• Nantucket Looms: Hand-woven textiles in colors borrowed from the island—fog grey, cranberry, sea glass green. Yes, the prices reflect the craftsmanship.
• Four Winds Craft Guild: Handmade Nantucket lightship baskets, the island's signature craft.
• Artists Association of Nantucket: Gallery showcasing local artists in rotating exhibits.

For Unique Finds

• Vis-a-Vis: Eclectic mix of gifts, home goods, and finds you didn't know you needed.
• Zero Main: Contemporary home design in a historic building.
• Force 5 Watersports: Everything for beach and water adventures.

Where to Eat Downtown

Downtown Nantucket punches well above its weight in dining. Within a few blocks, you'll find restaurants that could hold their own in Boston or New York—plus casual spots serving honest food done exceptionally well. What sets this apart is the seafood: much of it arrives daily from local waters, sometimes hours from ocean to plate.

For Waterfront Dining

Cru - Straight Wharf
The lobster roll at Cru divides loyalties on this island. It's Connecticut-style—butter-drenched, served warm—which purists from Maine will tell you is heresy. They're wrong. The sweet brininess of Nantucket lobster stands up to warm butter in a way Maine lobster can't. Add the harbor view, a glass of Sancerre, and that first bite of toasted split-top bun, and you'll understand why people wait 45 minutes without complaining.

Straight Wharf Restaurant - Straight Wharf
Fine dining with a view. The menu changes with what's available from local boats. Reservations essential.

For Casual Excellence

The Proprietors - India Street
Don't skip the raw bar. The oyster selection rotates based on what's harvested that day, and the staff can explain the flavor profile of each variety. Ask your server about the day boat scallops if they're available.

Dune - Broad Street
Seafood-forward menu in a beautifully designed space. The fish tacos at lunch are legendary.

For Quick Bites

Something Natural - Cliff Road (short walk from downtown)
Sandwiches on fresh-baked bread, served on a lawn under the trees. Cash only, worth the walk.

Wicked Island Bakery - Centre Street
Morning pastries and coffee that fuel many an island morning.

For Special Occasions

The Pearl - Federal Street
Asian-influenced coastal cuisine. The space is stunning, the cocktails creative, the food exceptional.

Ventuno - Federal Street
Northern Italian in an elegant setting. The handmade pasta is what brings regulars back season after season.

Practical Information

Getting to Downtown

If you arrive by ferry, you're already there. Both Steamboat Wharf (Steamship Authority) and Straight Wharf (Hy-Line) deposit you directly in the heart of downtown. Walk off the boat, and within two minutes you'll be on Main Street.

If you're staying outside of town—in Sconset, Madaket, or a beach area—the NRTA Wave shuttle connects to downtown regularly throughout the day. Biking in is also easy; dedicated paths lead to town from most directions.

Parking

Here's what the numbers tell: downtown parking is limited and expensive. The town has several small lots, but they fill early in summer. The reality is that you're better off without a car downtown. If you must drive:

• Broad Street Parking Lot: Closest to ferries, fills by 9am in summer
• Salem Street Lot: Short walk to town center
• Beach Street Lot: Overflow option, longer walk

Better approach: Park at your accommodation or a remote lot and shuttle or bike in. Your blood pressure will thank you.

Getting Around Downtown

Walk. Seriously. Downtown Nantucket is entirely walkable, and that's how you'll discover its character. The cobblestones are uneven—skip the heels and choose comfortable shoes with good soles. Bring flats if you want something dressier for dinner; most locals change shoes.

Restrooms

Public restrooms are located at the Steamboat Wharf ferry terminal and near the visitor center on Federal Street. Most restaurants and shops reserve facilities for customers.

Best Times to Visit Downtown

• Early morning (before 9am): Coffee, quiet streets, locals starting their day
• Mid-morning (9-11am): Shops open, manageable crowds
• Late afternoon (4-6pm): Golden light, happy hour starting, the day's energy shifting
• Evening: Dinner crowds, strolling couples, festive atmosphere

Avoid midday in peak summer if you want a more relaxed experience—that's when ferry arrivals peak and the streets are busiest.