Wellfleet,Massachusetts

• More about your oliver guide: Rachel Wynne
• Trip type: Family, Beach
• Activity level: moderate
• Ideal length of trip: One to Two weeks

to & from

During the summer there are regular Cape Air flights from Boston Logan and Provincetown Airport but better still, take the 90-minute ferry from Boston run by Bay State Cruise Company and Boston Harbor Cruises at the South Station. Provincetown to Wellfleet is a 20 minute drive. Drive from Boston.

Where to Stay

Rent a home. Wellfleet offers every accommodation from Cape Classic to 50s Modern.

Where to Eat and Drink

Wellfleet has an assortment of dining options. From tasting menus to clam shacks, you can get anything you want in this beautiful little Cape town.

• CERALDI:  offers a seven course, prix fixe, waterfront culinary experience at our intimate 45-seat space. Chef Michael D Ceraldi and team use premium local ingredients to tell the stories of the coastlands of Cape Cod. One of the best dining experiences I have had on the outer Cape (or really anywhere). Reserve early.
• Mac’s Shack: An institution on the Outer Cape. Mac and his brother Alex have a handful of restaurants and markets that serve up the freshest catch. Indoor/Outdoor table service at Mac’s Shack and window service/picnic style at Mac’s on the Pier. Don’t miss their fish market as well. We love their sushi, raw bar and fried oyster cob salad. No reservations. Go early.
• PB Boulangerie:  Chef Philippe Rispoli, a native of France, has established a fantastic French restaurant and bakery. Classic French dishes with a local Wellfleet spin. The bakery is out of this world- morning lines out the door for hot croissants.
• Winslow Tavern:  In the heart of town, pretty spot for a casual meal.
• The Pearl:  For a roof deck cocktail.
• Bombshelter: Local dive bar. Hard to find and no website. Really local. Hint it is near Wellfleet Bookstore & Restaurant on Kendrick.
• Bol of Love: Incredibly fresh and fantastically colorful smoothie bowls, smoothies and more. Stop here to fuel up before a day at the beach.
• Emack and Bolios: The best ice cream in town.
• Hatch’s Seafood and Produce: Visit fish and produce market for the freshest local catch and veggies. ‘Our fish comes from local Cape Cod waters, hand selected off of “day boats,” who bring in fresh fish every day to the ports of Wellfleet, Harwich, Chatham, Truro, and Provincetown.’
• The Flying Fish: Super casual and fun spot for breakfast and serves great pizza in evening. During the summer months they have live music mid week.

What to Do

Like many other Outer Cape towns the main attraction is the beach. Wellfleet has many to choose from. Some require a beach sticker for entry and some are pay by day. Check out guidelines here. 

There are also many beautiful ponds to swim in. When not at the beach, shopping and strolling around downtown Wellfleet is a great option.

• • Swim: White Crest Beach is a beautiful beach with towering sand dune cliffs. For pond swimming, Great Pond, 500 Cahoon Hollow Rd.
  • Shopping:
    • Salt- a carefully curated space featuring clothing, jewelry, and accessories;
    • Periwinkle–  Accessories and beach themed decor for indoor and outdoor living. Great house warming gifts;
    • Jeff Soderbergh- Custom Sustainable Furnishings.
    • Sustainable heirloom pieces worth a visit to his studio; Karol Richardson–  is both contemporary and easy;
    • AIM Thrift Store- 305 Main Street, amazing finds! Check hours as they are a bit all over the place;
    • Abiyoyo- https://abiyoyo.shoplightspeed.com Great little toy store, they also sell Wellfleet t-shirts and sweatshirts.

Sick Day Surf Shop https://www.sickday.cc Great spot to pick up all of your water gear.
Drift https://www.driftwellfleet.com Wonderful home goods. Great hostess gifts.
Farm Projects http://www.susienielsen.com Art and Design collaborations. Modern and inspiring works on display.

• Galleries: There are many galleries to pop into when in town. These two are my picks- Harmon Gallery- Contemporary well curated collections on the water; Left Bank Gallery– Established in 1971 in Wellfleet, a great place to view local artists.
• Drive In: A trip to Wellfleet is not complete without a trip to the drive in!
• Farmer’s Market -Wednesdays in town May-October.
• Theater: Wellfleet Harbor Actors Theater Great summer stock productions.
• Golf and Sail: Public golf course and weekly sailing lessons (for kids).
• Swing your Partner: Every Wednesday night in July and August, the town holds a square dance at the town pier parking lot from 7-9:30 p.m. The dance is free and all ages are welcome.
• Wellfleet Bay Wildlife Sanctuary: Hundreds of acres of marsh, beach and woodlands with five miles of trails, fun programs and a great visitors center.
• Yoga and Wellness: Quiet Mind Studio- great classes and massage.
• Wellfleet Oysters: Try them locally!
• Music: Beachcomber-Perched on a dune the Beachcomber serves lunch and dinner. However is more known for live music in the evenings all summer long.
• Run: The annual Wellfleet Road Race is a great event. Adult 5 mile course and Children

inside scoop

Take a Modern House tour or even better stay in one! Truly magnificent 50s modern homes scattered throughout the dunes and pine scrub of the Outer Cape. The Hatch Cottage is my favorite. The Cape Cod Modern House Trust (CCMHT) was founded to collect, archive and share documentation of the outer Cape’s exceptional modern architecture, restore a group of important, endangered modern houses, and to relaunch them as platforms for new creative work. https://ccmht.org/about/

skip it

Big hotels along Route 6. Stay in town local.

What to Pack

Beach casual. The evenings can be chilly so bring some warmer layers for beach fires.