11 Gems to Explore on Cape Cod this Summer

I grew up spending at least one week of every summer on Cape Cod. When I was really little my grandparents rented the same house in Dennis every year. We'd all pile in - grandparents, parents, aunts, uncles, toddlers and babies - for a week of beach days, seafood dinners and late night ice cream. 

When I was in elementary school we started to stay further out in Truro. My parents, sister and I have been staying in the same house for over 20 years. We'll be going back for the whole last week of July and I can't wait.

I've gotten to know the Cape very well, so today I thought I would share some of my favorite spots for those who are planning trips or will be exploring the area for the very first time this summer. 

The places are listed in order of proximity to Boston, starting with the closest. 

1. Quissett Harbor (Falmouth, MA) - The first time I visited Quissett Harbor was in 2013 as part of a bachelorette weekend. All the girls followed the bride down the walking path to the exact bench where her now husband proposed. It was so clear why he picked this spot. The walk is easy and enjoyable and the lookout point at the end of the trail is breathtaking. 

Quissett HarborQuissett HarborQuissett HarborQuissett Harbor

Anyone can visit Quissett. There is no sticker required or admission fee. 

2. Captain Frosty (Dennis, MA) - As little kids we always stayed at our grandparents rental house in Dennis. All three generations slept under the same roof and we traveled as a pack. Every night after dinner we would walk to Captain Frosty and wait in line at the ice cream window for dip tops.

In addition to ice cream, Captain Frosty serves all the traditional Cape Cod seafood and fried goodies. Even though we stay in Truro now, we always try to stop on the drive down or the way back home. Here are my sister and brother-in-law posing with the sign a few years ago. 

Captain Frosty

3. The Beachcomber (Wellfleet, MA) - The Beachcomber is one of the best known bars on the Outer Cape. It sits right on the sand of Cahoon Hollow Beach and has a huge outdoor bar and patio. Most nights they also have live music. After a long day at the beach this is the perfect place to unwind with mixed drinks, seafood platters and the sand between your toes. 

The BeachcomberThe BeachcomberThe BeachcomberThe Beachcomber

4. Flying Fish Cafe (Wellfleet, MA) - One of the things I love most about Cape Cod is that almost every restaurant has an outdoor patio or deck. The deck at Flying Fish Cafe has a mix of tables and Adirondack chairs, offering plenty of places for family to stretch out (and pig out!). All of the food at Flying Fish is excellent, from the bakery pastries to the packed sandwiches to the burgers with crazy toppings and the decadent desserts.

Flying Fish CafeFlying Fish CafeFlying Fish CafeFlying Fish CafeFlying Fish Cafe

Last year we decided to have lunch here as our final outing before driving back to Boston. It's just one turn off Route 6, making it super easy to stop in. 

5. Sunbird (Wellfleet, MA) - Right along Route 6 in Wellfleet is a food truck called Sunbird. Though they cook in a truck, the Sunbird team has set up an entire outdoor experience including tables and chairs, artwork and books for guests to read while visiting. 


Though it's not pictured here, I highly recommend the breakfast sandwich. They make it with bacon, but if you ask, they will happily make a vegetarian version.

6. Artichoke (Wellfleet, MA) - Directly next to the Sunbird truck is another truck called Artichoke. The team that runs this clothing store on wheels sells all of kinds t-shirts and tank tops each with a different Cape-centric design. 


7. Great Hollow Beach (Truro, MA) - This is the beach closest to where we stay each summer. It has the classic Truro look of high dunes dotted with tall green grass. On a clear day, you can see the Provincetown monument perfectly from your beach chair. This beach faces the bay (not the ocean) so we prefer to come at the end of the day and take long walks while the sun is setting. 

Great Hollow BeachGreat Hollow Beach

8. Head of the Meadow Beach (Truro, MA) - Head of the Meadow is another Galler family favorite. Best known for it's afternoon sand bar (created at low tide) this beach often has groups playing volleyball, people in the water surfing and kids running along the shore as the waves break over their feet. Major bonus: there is usually an ice cream truck camped out in the parking lot. Last year they also added a free library where residents and visitors could add books or take a book to read on the beach. 

Head of the Meadow

9. Chequessett Chocolate (Truro, MA) - This sweet addition (pun intended) popped up in Truro just a few years ago. The chocolate shop sells beautifully packaged chocolate treats in exotic flavors, but they also offer coffee, tea, juice and smoothies. Last year they started hosting a Mexican food truck in their parking lot, so now you can have lunch, quickly followed by dessert.

Chequessett ChocolateChequessett Chocolate

Here I am last September enjoying one of their chocolate shakes for breakfast. 

Chequessett Chocolate

Chequessett is open seven days a week and is directly across the street from the Truro post office if you'd like to send a postcard to your friends to brag about all the fun you're having. 

10. Truro Vineyards & South Hollow Spirits (Truro, MA) - I have a few happy places - Jamaica Pond, the Highline in New York City, the Fairchild Tropical Gardens in Miami, the boardwalk along the beach in Tel Aviv and Truro Vineyards on the Cape. From the very first time I visited I fell in love. The property is gorgeous, the wines are delicious and the staff is friendly as can be. 

Truro VineyardsTruro VineyardsTruro Vineyards

If it's your first time visiting definitely do the wine tasting and the vineyard tour. Afterward, bring your wine to the picnic tables outside and enjoy. 

Truro Vineyards

This past year for my 31st birthday I went with friends and we packed a huge spread of cheese, crackers, pickles, nuts and chocolate. I think we sat at that picnic table for three hours!

Truro Vineyards

A few years ago the vineyard also opened South Hollow Spirits, producing their own rum. Now they have a bar on the vineyard grounds that serves all kinds of delicious (and strong) rum cocktails.  

South Hollow Spirits South Hollow SpiritsSouth Hollow Spirits

If you'll be on the Cape this summer, even just for a day, Truro Vineyards & South Hollow Spirits is an absolute must. 

11. Commercial Street (Provincetown, MA) - Commercial Street is the main drag in Provincetown, the very last town at the tip of the Cape. The street is a long row of art galleries, shops and restaurants with outdoor patios and water views. 


We tend to wander up and down Commercial Street at night (because we don't want to give up valuable beach time), but if you're on vacation for a full week, it's fun to spend a day bopping in and out of shops. 

For those who may be wanting to experience the Cape but don't have a car, you can take a ferry from Boston right to Provincetown and it drops you off in the center of Commercial Street. 

There you have it! My list of 11 hidden gems to check out on the Cape this summer. Tell me, do you have a Cape go-to that I should visit during my trip next month? I would love to hear your suggestions.


Bianca Garcia's picture

Love this. Matt and I must make plans to go to Captain Frosty's this summer!

Molly's picture

You must! Excellent fried seafood, onion rings and of course, ice cream!

Lorianne Lacey's picture

Truro Vineyards is on my must-see list! Great ideas :)

Molly's picture

I know you would absolutely love it! It's impossible not to!

Olivia Beane's picture

Wow, whelp... I now have an impossibly strong desire to go to the Cape. I haven't been in YEARS! That sandwich with the avocado all but made me drool onto my desk.

Molly's picture

You and Nic should do it as a day trip! Flying Fish Cafe is the real deal (especially that sandwich).

Kristen Fenton's picture

so much excitement for this post. It's a real shame I haven't been to the Truro Winery though. Captain Frosty's is 1 minute from where I grew up so we went all the time :)

Molly's picture

You absolutely must do Truro Vineyards! You would love it. And I had no idea you grew up so close to Captain Frosty. I bet we waited in line near each other as little kids!

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Molly Galler

Welcome to Pop.Bop.Shop. My name is Molly. I’m a foodie, fashionista, pop culture addict and serious travel junkie. I’m a lifelong Bostonian obsessed with frozen confections, outdoor patios, Mindy Kaling, reality television, awards shows, tropical vacations, snail mail and my birthday.

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