Summer Fun: Cape Cod in 36 Hours

My family always goes on one big vacation a year—indeed, often only goes on one real vacation a year, and ever since I was a tiny baby, that vacation has been to Cape Cod, Massachusetts. When my mom was a kid she used to spend her whole summers down there, although for my own childhood, we usually made do with a two-week interval, the only major time I'd spent away from home probably up until I went to college. Now that I'm a nominal grownup with a full-time job, my own apartment, and cats to look after, I don't spend the whole two weeks with my family, but I still manage to get down for a weekend or so every year. And I've been going long enough that I have some pretty strong opinions about what you should do if you find yourself on the Cape, so today I'm going to share some of those. This might be a bit much to actually tackle in one 36-hour visit, but let's be ambitious, shall we?

Logistics Note: For the past decade-plus, my family has been staying in Orleans (approximately 90 miles from where I live in Cambridge), which is part of what is usually called the Lower Cape (left-hand image), so this post will be strongly skewed toward the area around there and the Outer Cape (right-hand image), and will therefore feature a limited sample of the whole wealth of options the Cape has to offer. Also, I'm writing this for visitors who are going "in season," that is, sometime from May to September. The Cape is also lovely in the off season, but there's less to do and the ocean is much, much colder (not recommended). None of the things I have to recommend are super secret or off-the-beaten path, but I have personally vetted them all and as a person with 29 years of Cape experiences under my belt, I think they're all worth your time if you're visiting.

First, and Most Important: FOOD
There is SO MUCH food to choose from on the Cape. Much of it revolves around ridiculously fresh seafood, which is actually not my thing, but if it is your thing, you'll have no problem finding it. For those who appreciate non-seafood options, a few great choices in Orleans:

I think I have been to the Ho at least once every year since I was born. This place is an institution. A few words of advice: There are no reservations, just put in your name and wait for a table. Wait in the bar area if that's a thing you'd like to do. Try to get the bartenders to ring the bell for you. One way to do this is to tip well. Another is to bring your mom who is very friendly and will flirt with the bartenders, especially Abe. Order off the daily specials chalkboard. The kale soup is delicious. Actually read the signs on the walls. It may look and feel like a TGI Fridays gimmick at first, but every bit of bric-a-brac there is actually meaningful, and some of it is quite funny. If you ever find yourself on the Cape in the off season, Land Ho! will be there for you—I've been there in the snow in the dead of winter and it was still delightful. No matter when you go, you can meet some pretty great characters at the bar. Plenty of locals frequent this place along with the summer tourists.

From an old stand-by to a brand-new favorite...Sunbird Kitchen just opened this summer, the first brick-and-mortar outpost of an existing Cape food truck. I was in love the moment I stepped inside. The space has an incredibly warm and inviting aesthetic with a great silly, witty sense of humor in its details. The food is really terrific—hearty and delicious and wholesome. So far they are mostly focused on breakfast, lunch, and "evening bites" but they also serve wine and beer and I have to assume that a more structured dinner menu is in the long-term plan. I went for both lunch and breakfast while I was there, I liked it that much. I honestly wish there were a place like this in my neighborhood at home; I think I'd basically live there. I can't wait to go back.

This one is both food and entertainment. In my childhood memories, the bowling alley in Orleans was a dim, musty place that you only went to as a last resort on the most disheartening of rainy vacation days. That has all changed in the past few years—now under new management, the bowling alley is well-apportioned, charmingly retro, and accompanied by a really solid barbecue restaurant and fully stocked bar. You can eat delicious food and get seriously tipsy all while bowling a few frames of that delightfully Massachusetts game, candlepin (the balls are tiny and the pins are weird and it's basically impossible but it can be pretty fun). Highly recommended even if it's not raining. 

This can be a divisive topic on the Cape, but for my money, the best in the Lower Cape area is to be found at the Ice Cream Cafe (conveniently located right next to the Cottage Street Bakery, which has the most ridiculously delicious doughnut muffins you'll ever eat, called Dirt Bombs—sometimes the Ice Cream Cafe even makes a flavor featuring the muffins, which is like deliciousness inception).


Duh. The Cape is basically one giant sandbar, so of course you should go to the beach. The three photos above are of Skaket Beach in Orleans, which is a great beach right at the "inner elbow" of the Cape which means it has the best tides—at low tide you can walk out almost a mile and find all kinds of treasures and creatures and at high tide there's pretty great swimming. There's also an excellent snackbar and very serviceable bathrooms. The ocean side beach (Nauset Beach) may be more appealing to those who want cold, deep Atlantic water and real waves (plus the added bonus of possibly spotting a seal, or a shark), but for my sunbathing, sandcastle-building ways, it's Skaket all the way. 

Orleans has many delightful little shops (my favorites are the cluster of stores in the Earth House building on 6A), but on the whole, the better shopping is to be found further out, particularly at the very tip of the Cape in Provincetown. If you're headed that way, I strongly suggest a stop at the Atlantic Spice Company retail store in Truro. It's one of the greatest, most wonderful-smelling places in the universe. And Provincetown has some of the best people-watching in the world, so make sure you take a trip out there—evenings are best in the summer. The other excellent shopping destination that I hit up pretty much every year is the Wellfleet Flea Market. It's different every time and I've actually found some pretty great treasures, as well as some pretty hilarious junk.


  • The Atlantic White Cedar Swamp Trail and Marconi Wireless Site in Wellfleet are worth a visit for some Middle-Earth-like vibes in the former and a bit of historical import mixed with amazing views at the latter. 
  • The Wellfleet Drive-In Movie Theatre is what the flea market site turns into at night. It's high on kitsch and you can get a double feature for $9. I advocate nominating a designated driver and smuggling in some adult concessions for the rest of the passengers in your vehicle. 
  • The Edward Gorey House is a tiny little museum made out of Gorey's old house in Yarmouth Port. Gorey is one my favorite illustrators and has been for a long time, and this museum is really charming and quirky. Also has an excellent little shop. (I like a little shop.)
  • I don't have many recommendations in the way of accommodations, since when I'm on the Cape I usually stay with my family (in a rental house), but on odd weekends I have stayed at The Cove Motel in Orleans and at the Nauset Knoll Motor Lodge in East Orleans and found them both completely serviceable and mostly charming. There are much ritzier places to stay (and much more rustic places, as well—camping in Nickerson State Park comes highly recommended) but I'm of the opinion that you probably shouldn't spend too much time at your lodgings apart from sleeping and the occasional shower, so they don't need to be crazy awesome.

I hope this post will be helpful to anyone planning a trip to the Cape, whether it's a short weekend getaway or a longer beach vacation. Let me know in the comments if you go and try any of the places I've recommended, or if you have other thoughts about the best things to see, do, and eat on Cape Cod!