Picture this – you’re driving over a long, narrow bridge as the sun sets, the ocean glistening down below you on either side. You can feel your worries fade away with the view of the mainland in your rear view mirror, with a hydrangea-speckled weekend of sandy beach days, lobster rolls, seaside sips and extra large ice cream cones in your near future. How, you might ask, can you make this dream a reality? By visiting Cape Cod, of course!
The Cape, widely hailed as the go-to beach destination for Massachusetts residents far and wide, is still relatively new to me. My mom moved down from Maine just last summer, but with beautiful, soft-sanded beaches, quaint downtown streets, a plethora of fun activities, and more than its fair share of New England dream homes, it has quickly become one of my favorite places. And after getting to share it with some of my favorite people this summer, I thought I would document all that encompasses the best Cape Cod weekend EVER. If you’re looking for your quintessential New England summer experience, look no further!
Now before we get started, let’s address an important factor – where you should stay. Each town has its own charm and activities to offer, whether you’re in Falmouth or the Outer Cape or anywhere in between. My Mom lives in Barnstable, which is very centrally located and where this itinerary is based off of, but I’ve also spent a fair amount of time in Orleans with my boyfriend and love it there so much – you really can’t go wrong wherever you end up!
Now let’s talk strategy – I’m outlining a weekend escape here, but if you are hoping to spend even more time on your vacation, the world is truly your oyster. I’ll include some additional recs later so you can explore to your heart’s desire!
So without further ado, here is my suggested weekend itinerary on Cape Cod:
Thursday
- Take a half day and drive down to the Cape from Boston – note, there will be traffic. I highly recommend leaving significantly before or after 5pm.
- Grab an early dinner at Chart Room – and by dinner I mean lobster roll, of course. There’s usually a wait, so the earlier the better! Bonus points if you stick around for sunset drinks outside after.
- Treat yourself to some ice cream from Four Seas right down the street.
- Head home and rest up for a wonderful, sunshine-filled weekend ahead!
Friday
- We’ll keep it local today, starting off with what I view as Barnstable’s crown jewel – Nirvana Coffee. Grab yourself an iced latte or a donut – or both – and you won’t regret it!
- Next, it’s time to find your beach – my personal favorite is Dowses, but you do need a resident sticker to park there. If you don’t have one, have no fear! There are plenty of public beaches to pick from as well. Grab some sandwiches – I’ve practically tested the whole menu at Fancy’s Market and I’m a big endorser of their tuna wrap, which I recognize is a hot take – and go soak up some sun!
- Next up on the list is dinner at one of my favorite spots, Crisp. They don’t take reservations either, so definitely head there on the early side. But if there is a wait, there’s a cute outdoor bar to wait at and enjoy all the frosé you could want! Make sure to order the garlic knots and brussels sprouts to start, and I can’t recommend the angry beekeeper flatbread enough.
- Last on the list for today, head to The Port for drinks – notably, mudslides of all shapes sizes and flavors – and enjoy three different bars, live music, dancing!
Saturday
- Today, we’re doing it all. To start, you guessed it – we’re heading back to the beach! Pick the spot closest to you – for me, this is usually Long Beach, but this one does also require a resident sticker – and enjoy some swimming and sunshine all morning.
- Head home to shower, change, rest, relax and recharge for a bit, then embark on a journey to Chatham for the afternoon and evening. I highly recommend stopping in at the Fish Pier to see the seals that frolic near the boats, then heading downtown to stroll, shop to your hearts’ desire, and grab some ice cream – or candy, or fudge, or whatever else you’re feeling – they’ve got it all!
- Next up is arguably the most scenic part of our itinerary. Head to the Bayview and Chatham Bars Inn Terrace for happy hour with a view. This one speaks for itself.
- You’ve probably worked up quite an appetite, so I highly recommend sticking around in Chatham for dinner – you can stay at CBI to eat at The Beach House or head back into town for sushi at Bluefins or a more classic seafood dinner at Captain’s Table or The Impudent Oyster. So many choices, so little time!
- Last but certainly not least, grab some late night drinks at The Squire and dance the night away!
Sunday
- And just like that, the weekend comes to a close. Head to your closest beach and soak up the sun before you head home – and again, don’t underestimate the traffic.
Sounds like the best weekend ever, doesn’t it? And if you’re like me and just can’t get enough, here’s a more comprehensive guide of things to do far and wide – obviously most concentrated around where I frequent!
Daytime Activities
- The Beach, of course. You can’t go wrong with any, but my personal favorites are:
- Dowses Beach – Osterville
- Long Beach – Centerville
- Sandy Neck Beach – Sandwich
- Lighthouse Beach – Chatham
- Nauset Beach – Orleans
- Coffee
- Nirvana Coffee Co. – Barnstable
- Snowy Owl Coffee Roasters – Sandwich, Brewster or Chatham
- Lighthouse Keeper’s – Yarmouth
- Old Kings Coffeehouse – West Yarmouth
- Scenic Strolls
- The Knob
- Shopping
- Mashpee Commons
- Most downtown areas – the best spots are Falmouth, Chatham and Ptown
- Day Trips
- Chatham
- Ptown
- Martha’s Vineyard or Nantucket
- Ice Cream
Drinks
- Cape Cod Winery – Falmouth
- Bad Martha’s – Falmouth
- Tree House Brewing – Sandwich
- The Port – Harwich
- Chatham Bars Inn – Chatham
- The Squire – Chatham
- The Woodshed – Brewster
- The Beachcomber – Wellfleet
- Chapin’s – Dennis
Food
For Breakfast or Lunch:
- The West End – Brunch – Hyannis
- Pain D’Avignon – Brunch – Hyannis
- Amie Bakery – Breakfast/Pastries – Osterville
- Fancy’s Market – Sandwiches – Osterville
- Lamberts – Sandwiches – Osterville
- Sunbird – Breakfast Sandwiches – Orleans
- Hole in One – Breakfast – Orleans
- The Corner Store – Breakfast Burritos – Orleans or Chatham
- Nauset Farms – Sandwiches – Orleans
For Dinner:
- Fishermen’s View – Sandwich
- Estia – Falmouth
- Bluefin’s – Falmouth or Chatham
- Crisp – Osterville
- Chart Room at Croby’s – Osterville
- Anejo – Hyannis or Falmouth
- Naked Oyster – Hyannis
- Tugboats – Hyannis
- Baxter’s – Hyannis
- Spanky’s Clam Shack – Hyannis
- The Knack – Hyannis or Orleans
Whew! That’s all for now – I hope this guide helps make all of your New England summer dreams come true. Enjoy! ☼
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