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Harbor LIFE: Wellfleet

Wellfleet Harbor

Aerial of Wellfleet Harbor. Photo by Josh Shortsleeve

Hop back in your car and head down Kendrick Avenue and Chequessett Neck Road for a trip that’s worth a spot on a list of the Cape’s best short, scenic drives. Shortly after you cross over the Herring River, look to the left for a Cape Cod National Seashore sign for parking for the Great Island Trail. You can hike to the Great Island Tavern Site (1.8 miles). A longer hike to Great Beach Hill (2.4 miles) provides majestic views of Wellfleet Harbor and Cape Cod Bay.

Head toward downtown and take a quick but memorable detour just off Commercial Street onto Holbrook Avenue to Wellfleet Marine. This unique business has been renting and repairing boats for almost 70 years, but less known is their fish market and unique gift shop. It is nearly impossible to walk away without finding a perfect gift or treasure for your own home or garden.

A bit farther down Commercial Street, grab a bite at Mac’s Shack. Just look for the fisherman on the roof who’s reaching over his boat to haul in a lobster that’s about three times as long as he is tall. The galleries on Commercial Street, like Left Bank, Cove Gallery and Cherry Stone Gallery, all feature local art in a variety of mediums.

Wise harbor visitors will leave time for a stroll on Main Street to check out shops like Curiouser & Curiouser, with their unique trove of affordable and sustainable goods. Live entertainment and films can be found at the Preservation Hall throughout the year. Dinner on the way back to Route 6 at the Wicked Oyster is worth the trip alone and will leave you planning your next return visit; perhaps a weekend at The Wagner at Duck Creek next door.

Around Wellfleet:

Bookstore & Restaurant

Enjoy lunch and dinner daily with spectacular views of Wellfleet Harbor and Great Island from the outer decks. Menu includes Wellfleet oysters and littlenecks, native seafood, steaks, pasta dishes, sandwiches, salads and children’s favorites. Bomb Shelter Pub is open year-round 4 p.m. to 1 a.m. The bookstore has collector’s items.

50 Kendrick Ave 508-349-3154

Curiouser & Curiouser

Curiouser & Curiouser is a place where all kinds of good things come together. They have a mixture of the familiar with the exotic, the old with the new. A thing that finds its way into their shop is special. Curiouser & Curiouser is known for it’s made-in-the-USA and Fair Trade focuses with a unique curation of artisans and crafters presented in inspiring and thoughtful displays. Products sold are chosen based on craftsmanship, quality and uniqueness, as well as the happiness they bring. 

361 Main Street 508-214-0299 •

Mac’s Seafood

Mac’s Seafood serves fresh, sustainably sourced seafood and creative coastal cuisine at their Outer Cape restaurants and seafood markets. Mac’s Fish House & Market in Provincetown and Mac’s Market & Kitchen in Eastham are open year-round. Mac’s Shack and Mac’s on the Pier, their original market and restaurant, are open seasonally in Wellfleet.

PEARL Restaurant & Bar

Right at Wellfleet Harbor with panoramic views. Open from 11:30 a.m. May-October. PEARL is the quintessential Cape Cod dining experience with indoor and outdoor seating on multi-level decks, and an extensive menu specializing in local seafood. Happy hour menu with live local music 3-5 p.m. on select days.

250 Commercial Street • 508-349-2999

The Wagner at Duck Creek

Extend your trip to Wellfleet with a stay at The Wagner at Duck Creek. Past meets present at the three charmingly restored historic homes on the property. Enjoy picturesque views of the bay marsh and a laid-back meal at The Well Tavern + Kitchen, also the ideal venue for your special event.

70 Main Street 508-349-9333

The Wicked Oyster

The Wicked Oyster, located at 50 Main Street in Wellfleet. Serving breakfast and dinner year-round, with lunch in the “off-season.” From burgers to filet mignon, The Wicked O is the perfect place for every taste! Preview the menus and reserve a table at

Wellfleet Marine

Just around the corner from the Wellfleet Pier, this unique establishment has been serving visitors and residents for more than six decades. Their full-service boat repair and rental operation ensures you can get out on the water for a full day of adventure. An on-site fish market and intriguing gift shop make sure you have something to take home.

25 Holbrook Avenue 508-349-6417

Wellfleet Preservation Hall

Wellfleet Preservation Hall serves as a center for arts, culture and community connections. With over 600 year-round events ranging from weddings to concerts, yoga, dance performances and film festivals, anything can happen at the Hall! Located at 335 Main Street, in the heart of Wellfleet.


Hours for many businesses in Wellfleet change with the seasons, so be sure to check before visiting.

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