Cape Cod Highlights from a Long Weekend Away
From lobster rolls to paper shops - a few favorite finds from the south to the very tip of the Cape
As part of my recent trip to the U.S., I spent a long weekend in Cape Cod with my family - my second time there (third, if we’re counting when I was just a wee chick), but the first time I got to slow down and really explore. We drove up from New York, exploring small towns, hunting down roadside bakeries, and averaging a lobster roll a day.
I was surprised by just how wild parts of the Cape felt - pristine beaches, dunes that stretch on and on, and little pockets of untouched greenery that give the feeling you’re at the very edge of the world. It’s quite peaceful - not quite island time, but not far off - with enough local life, art, and food to keep you happily wandering.
We based ourselves in Chatham, a charming and well-situated town that gave us easy access to the eastern coastline and the tip of the Cape. We didn’t cover it all (Hyannis and the west are on the list for next time), but here’s a handful of spots we loved from our few days away.
Some notes:
We visited just before high season (Memorial Day to Labor Day), so not everything was open - but that meant fewer crowds, which we didn’t mind.
You definitely need a car to get around, not walkable but it’s bike-friendly if you’re up for it.
For more recs, I recommend the NYTimes 36 Hours on the Outer Cape, and 36 Hours in Provincetown (found by my fiancé-in-law (is that a thing?))
Here’s my Google Maps list with all the starred spots and a few extras.
And yes - play Walcott on repeat as the unofficial Cape Cod soundtrack.
Cafés + Bakeries
Who knew Cape Cod was a bit of a haven for coffee lovers? We came across SO many solid spots - from cozy small-town bakeries to specialty roasters, there’s a lot to love.
Our favorites:
📍Three Fins Coffee & Cacao (Chatham)
We went every day. Housed in a reconverted gym (the dining room is literally inside an old pool!), this place has great energy, excellent coffee (roasted in-house), and the best gluten-free muffins I’ve ever had. Don't be thrown off by the all-black exterior - it’s full of personality inside. Also a location in Dennis.
📍Cottage Street Bakery (Orleans)
Cuuuute. Home of the famous dirt bombs, this place is tiny but buzzing with locals. We only popped in for pastries, but we wished we had more time (and the appetite) to stay longer. Definitely regretted not trying the bisque.
📍Relish Bakery & Sandwich Shop (Provincetown)
Go early for the blueberry muffins - soft, buttery, so SO good. The sandwiches also looked amazing, and the staff were lovely. Great stop before hitting the town or beach.
Other noteworthy spots:
Liberty Artisanal Bakery (Chatham): Cute for a quick pickup. Their selection rotates almost daily, and the bread looked mmm mmm good.
Snowy Owl (Chatham + Brewster): We didn’t make it this time, but it’s saved for next round - I mean if the Reddit thread recommends it, you gotta go, right?
Eats + Sips
Cape Cod has a lot of dining options - though it can be tricky to figure out what’s worth it and what’s just riding the high-season tourist wave. Prices run high, and some places can feel a bit too commercial. But we found a few gems - simple, relaxed, some might even say we had the best lobster rolls of our lives.
Here’s where we’d go back:
📍Mac’s Chatham Fish & Lobster (Chatham)
A sun-soaked lunch here was one of the best parts of the trip. The lobster roll was perfect - buttery, flavorful, not too heavy. Sit outside, soak up the sunshine, and let the roll do the talking.
📍Mac’s on the Pier (Wellfleet)
Another standout lobster roll, this time with full-on seaside shack vibes. It’s right on the water - casual, no frills. (Side note: is every shack owner on the Cape named Mac?)
📍Moby Dick’s (Wellfleet)
More of a sit-down spot, but still laid-back. On the edge of town, so likely packed in the summer months, but the food was hearty and the staff welcoming.
Other noteworthy spots:
Liz’s Cafe, Anybody’s Bar (Provincetown): Classic American breakfast done right, diner-style.
Hog Island Beer Co. (Orleans): The brewskies and food-truck-style bites look really good.
Truro Vineyards (North Truro): On our list, but the weather didn’t cooperate. Feels built for a sunny, slow afternoon - hopefully next time.
Sweet Tomatoes Pizza (Chatham): Great for a casual night in. Thin crust, balanced toppings, not too oily - we were pleasantly surprised. Even as self-confessed New York pizza snobs, this one got a thumbs up.
Local Shops + Treasures
Cape Cod is full of shops - but truthfully, a lot of them lean toward the usual tourist fare: overpriced, same-same trinkets, and not much in the way of local charm. But tucked in between, we found a few really special spots.
Here’s where we found the good stuff:
📍The Customs House Fine Papers (Wellfleet)
A true gem. Thoughtfully curated paper goods, cards, notebooks, and small home pieces - everything felt intentional. Heidi, the owner, is lovely. We walked out with a notebook, a box, and a handful of cards we didn’t need but had to have.
📍Salt (Wellfleet)
A fashion boutique inside a beautifully converted house. Great mix of brands.
📍Perry’s Fine Wines & Liquors (Provincetown)
Great for stocking up on wines or picking up a beachside bottle, not your average liquor store.
Other noteworthy spots:
AIM Thrift Shop(Wellfleet): Proper little thrift shop - takes a bit of digging.
Provincetown is full of small galleries - some more affordable than others - that are worth exploring. We wandered in and out of a few that featured local artists, and even just window shopping felt inspiring.
Scenic Stops
One of the things that surprised me most about Cape Cod was just how wild and beautiful the landscape is - it’s expansive, almost cinematic.
Here are some of the places where that feeling really came through:
📍Race Point Beach (Provincetown)
Stunning. Just stunning. The drive alone - through the sand dunes - feels like part of the destination. You can bike, hike, or simply drive through, but don’t skip it. Feels beautifully otherworldly.
📍Wellfleet (the town + harbor)
We loved wandering around Wellfleet - it felt lived-in and local (more so than Chatham), with a touch of old-school charm. The harbor area is great for a walk, and the surrounding marshes and coastal roads give you that serene, slightly-salty, "you’re really on the Cape" feeling.
📍Provincetown
Provincetown is… an experience? Part artsy coastal town, part chaotic boardwalk. Commercial Street (especially the central stretch between Lopes Square and MacMillan Pier) can feel like Cape Cod’s answer to Disney World. But just a few blocks outside that core, the town becomes quieter and more charming: pastel houses, hidden galleries, locals tending their gardens. Worth the visit - just veer off the main drag for the best bits.
Other noteworthy spots:
First Encounter Beach (Eastham): Weather didn’t cooperate but looks great at sunset. Named for the site of the Pilgrims' first encounter with the Nauset tribe.
Lighthouse Beach + Chatham Light (Chatham): The beach here stretches on and on, with the lighthouse perched just behind you - classic Cape Cod.
Chatham Main Street: A blend of charm and a few too many touristy storefronts - but still worth a stroll.
Cape Cod, Until Next Time
Cape Cod is officially on the list of places I want to return to. Loved the mix of windswept nature with low-key local vibes. Even with just a few days, we felt like we got a real taste of the Cape’s personality.
If you’ve been and have favorite spots - food, coffee, beaches, trails, shops - I’d love to hear them!
As always, thanks for reading.
xx Anna
Oh this is making me want an East coast summer getaway so bad!!!
Love it! Your maps link isn’t working though