Provincetown (Ptown), Massachusetts
“It is the Morocco of America, the New Orleans of the north.” ― Michael Cunningham, Land's End: A Walk in Provincetown
- More about your Oliver Guide: Rachel Wynne
- Trip type: Adult, Beach
- Activity level: moderate
- Ideal length of trip: Long weekend
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.
Where to Stay
There are dozens of amazing small boutique hotels tucked away in Provincetown. I suggest checking out the location before booking- in town vs out of town. If you want quiet retreat do not stay in the heart of town.
Where to Eat and Drink
Restaurants come and go in Ptown. From fish shacks to high end dining, Ptown offers something for everyone.
- I like walking out to the West End in the morning and popping into small bakeries (http://www.ptownrelish.com) and boutique food markets for morning tea and pastries. Reservations are encouraged for the nicer spots in town.
- Joon Bar: We have had some nice meals at the bar. Local seasonal specials.
- Red Inn: Classic Cape Cod dining with a great view.
- Ciro and Sals: A Ptown classic, italian fare.
- Provincetown Brewing Co: Opened recently, casual off Commercial Street.
- Lobster Pot: What you see is what you get- if you want a lobster roll this is your spot.
- Mac’s Ptown: On the outskirts of town, Mac’s has become the defacto seafood spot on the Cape. Always consistently good. We like the sushi the best! And stop by their fish market next door for the local catch and great sauces as well as take away.
What to Do
Strolling Commercial Street is an activity unto itself. I prefer the outskirts of town. I particularly like walking in the West End where beautiful seaside homes are perched on the edge of the sea. The nightlife in Ptown is definitely geared towards the LGBTQ+ but can be enjoyed by all. There is never a lack of things to do in Ptown.
- Galleries:A few galleries not to miss: Berta Walker Gallery 208 Bradford Street, Four Eleven Gallery 411 Commercial Street, Provincetown Art Association and Museum (PAAM) 460 Commercial Street (great seasonally curated shows and also week long workshops)
- Climb Pilgrims Monument: 252-foot tower in the center of town with 116 steps built in 1907 to commemorate the 1692 arrival of the Mayflower. The Pilgrims’ first landing in the New World in Provincetown
- Whale Watch: Dolphin Fleet
- Sunset cruise: Bay Lady II or Hindu
- Bike: The Provincelands Bike Trail, a five-plus mile loop that takes you through forests, dunes and bogs. There are plenty of bike rental places in town.
- Herring Cove for sunset Pack a picnic from FarLand Provisions 150 Bradford Street Small corner store & deli featuring on-site bakery and prepared foods
- Take a Dune Tour: Art’s Dune Tours provides a off-road tour experience to our family of visitors through the heart of the National Historic District of the Cape Cod National Seashore Park.
- Shopping: The Provincetown Bookshop 246 Commercial Street , Marine Specialities 235 Commercial Street, Shor Home 240 Commercial Street, Captain’s Daughter 384 Commercial Street, Century 191 Commercial Street
- Dance!: Check out the famous Boatslip Tea Dance on the West End for some serious cardio. It’s a wild dance-a-thon that caters the to the LGBTQ+ community (but everyone's welcome!) and runs daily in season from 4-7 p.m.
Inside Scoop
Ptown is crowded, really crowded in the summer months. Go in September or October when the crowds die down and it is easier to navigate. If you are there in the summer months stay in the West End.
What to Pack
Anything goes in Ptown! We have seen it all from leather chaps to drag to speedos. We have also seen impeccably dressed men out on the town. It all depends on what you are there for. Casual day wear more dressed in the evenings.
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From lobster rolls to drag queens there is a little (or a lot) of something for everyone in Provincetown, MA. My childhood summers were spent one town over, when Provincetown was an art mecca and a somewhat sleepy Portuguese fishing town. Now there is nothing sleepy about Provincetown (unless you are there in December). Provincetown has become a summer gathering place for the LGBTQ+ community and it feels like celebration on Commercial Street everyday.
Still grounded in the arts- From the 1940s to the 1950s, Provincetown was a summer center of Abstract Expressionism represented by such painters as Franz Kline, Jackson Pollock, Lee Krasner, Motherwell, Helen Frankenthaler and Fritz Bultman, in addition to Hofmann. And more recently Mary Oliver, Joel Myerowitz, Michael Cunningham and John Waters (who I have been seated next to on Cape Air 8 seater flights) Provincetown is an eclectic mix of communities gathered on a small sand bar on the tip of Cape Cod.
Truro, Massachusetts
'The sea-shore is a sort of neutral ground, a most advantageous point from which to contemplate this world.' ― Henry David Thoreau, Cape Cod
- More about your Oliver Guide: Rachel Wynne
- Trip type: Family, Beach
- Activity level: easy
- Ideal length of trip: One or Two Weeks
to & from
Drive from Boston or 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 is 9 miles up the road).
Where to Stay
Rent for a week in Truro, but make *note* there is a difference between Truro and North Truro; staying in Truro you will not have to be on Rt 6 as much.
Where to Eat and Drink
Truro has just a few options for food and drink. We love our local market and restaurant. For more restaurants head out to Wellfleet and Provincetown.
- Jam’s Market: A Gourmet market with all of the essentials for a quick shop. Great sandwiches and baked goods for take away. It is a perfect beach town market.
- Blackfish: Really the only game in downtown Truro. Fantastic bar with friendly bartenders and always some sort of Boston team playing above the bar. The food is good and the atmosphere lively. I always order the lemon panko crusted sole with cauliflower mash and the dense chocolate cake with pretzel crust for dessert.
- Truro Vineyards: Up the road in North Truro heading to Ptown is Truro Vineyards and South Hollow Spirits (Rum and Gin). Really pretty place to visit. They have tours and you can picnic and play corn hole on their expansive lawn. They have a food truck and bar truck to sample the their libations.
What to Do
Think beach, beach and more beach in Truro…then throw in the occasional farmer’s market and studio visit and that sums up how summer flows on the Outer Cape.
- You need a beach sticker to go to most Truro Beaches. The local Beach office sells Resident and Non Resident beach stickers here.
- Due to shark activity in the area- Truro beaches are closely monitored for sharks and occasionally closed.
- Long Nook Beach- Incredible dunes and expansive beach. Depending on the year there can be great sandbars and pools at low tide.
- Ballston Beach- Beautiful and remote. My favorite beach on The Cape (or really anywhere).
- Corn Hill- (pay per day without sticker) Bay side beach. Can get crowded in summer months.
- Fischer Beach- Bay Side beach with a small amount of parking. Great place to watch the sunset. The Hopper house is perched on the hill overlooking this beach.
- Farmer’s Market- Downtown Truro (the market has moved to the Truro School for Summer 2020 due to Covid) every Monday Memorial Day to Labor Day Fantastic local produce, flowers, honey, lobster and much more. We stock up for the week here. There are also honor system Farm Stands all over town. The one on Longnook Road is great for tomatoes and I get my flowers from the stand on the right downtown as you approach the Rt 6 ramp heading south. Check out the incredible Sustainable Cape for more info about Farmer’s Markets up and down the Cape. Labor Day they host a very popular Agriculture Fair.
- Golf Highland Links- Deep natural rough, Scotch broom, heath, non irrigated open fairways, and spectacular ocean views keep the course a genuine links, as close to the Scottish tradition found anywhere in the eastern United States.
- Live Music- Check out the Payomet for their fantastic summer music series.
- Jobi Pottery https://jobipottery.com In North Truro off of Route 6, worth checking out this iconic pottery studio and gallery established in 1953 in Truro.
- Accent on Design Tucked away behind Jams in downtown Truro. This amazing little store has everything from one of a kind vintage jewelry to beautiful home furnishings. Amy, the shop owner, has an incredible eye and is very welcoming.
Inside Scoop
Check out the arts in town! Edward Hopper spent over 40 summers in Truro- ‘Hopper painted the Outer Cape’s ineffable light.’ Since that time many artist have become residents of this town or spend summers capturing the ‘Cape Cod light’. Open studios are the best way to view local artists works.
- Thomas A. D. Watson a year round resident of Truro paints incredible realist depictions of seascapes and outer Cape life. His studio is definitely worth a visit. Tuesday/Thursday 9-12 and by appointment 508.349.1631 http://thomasadwatson.com
- Amy Wynne, a painter, has been coming to Truro her entire life. Mostly painting plein air keeps her process fresh and recharges her color perception. You can often see her with her easel out in the elements in Truro. She also offers workshops in Truro. By appointment only. 401.651.6281
- Truro Center for the Arts at Castle Hill has served a single purpose for more than 45 years: to create an inclusive and supportive arts community by providing a wide range of artistic experiences to students at all levels of ability. Weekly classes in painting, photography, printmaking, sculpture, ceramics, photography, jewelry and writing.
What to Pack
Bathing suits, flip flops, beach dresses, hats and sunscreen. Life is very casual in Truro. I did not realize my daughter had lost all of her sandals over the summer when we were departing for our Cape flight- so barefoot living is more than acceptable!
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Truro’s land is 75% designated National Seashore (thank you President Kennedy) , Truro is one of the most pristine and undeveloped little towns on the East Coast. Downtown consists of a Post Office, Gourmet Market and a restaurant- nothing more, nothing less. My dad always says- ‘blink and you will miss it.’ It is slow living in Truro, and that is the way we like it.
Wellfleet,Massachusetts
Swing down to Mac's Shack for fresh oysters and a Devil's Purse to wash it down.
- 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.
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- 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/
What to Pack
Beach casual. The evenings can be chilly so bring some warmer layers for beach fires.
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