Hello from Cape Cod! I am on vacation this week, so will be recirculating some of my most popular posts from over the years all week long. As I’m here on the Cape and always get asked for recommendations for what to do, where to stay, and so on and so forth, I thought it would be fitting to kick off the week with my Cape Cod travel guide.
Cape Cod Travel Guide
Many of you know that I grew up in Dennis, Massachusetts (a small town in the middle of Cape Cod.) One of the questions I get most is where to go on the Cape… so I thought I’d put together a little guide for you. I originally published this piece in 2014 but have kept it updated over the years. (last update: July 2021)
I am obviously a little bit biased here as I grew up in Dennis, so naturally I think that Dennis is the best part of the Cape. Everyone who is from Cape Cod thinks that their town has the best beaches, but Dennis actually does (sorry, Chatham and Orleans.) And the best beach in Dennis (far and away) is Mayflower Beach. Really, it is just the best beach ever. You’ll see when you get there, but it’s my happiest place. Stretches of powdery white sand and when the tide goes out it feels like the beach just goes on and on forever. If you have four wheel drive, go to Chapin Beach. It’s right next to Mayflower but really fun to drive onto.
Lunch & Snacks:
The Merc in Dennis Village has the yummiest sandwiches ever. I’ve been known to stop in for iced coffee (their coffee is really good), sandwiches (and sometimes a China cookie) before a day at the beach. I’m partial to “The Veggie” on multigrain. It’s the most scrumptious, filling sandwich… every vegetable you can imagine with havarti cheese. My mom is a big fan of the chicken salad + apple sandwich. The broccoli salad is also to die for. They’ve been making it for decades (seriously) and it’s always exactly the same — incredible.
Sesuit Cafe in East Dennis makes the best lobster roll you will ever eat. It’s expensive (around $18, I think?) but it basically has an entire lobster in it. (see below photo!) It’s an absolute must-do while you are visiting. It’s BYOB, so pick up a bottle or two of wine beforehand and have a little picnic. Our favorite thing to do is sit at the raw bar and order oysters + littlenecks. They’ll also let you order a lobster roll there which means skipping the line. There are only 5 seats so it can be hard to get a spot but if you do, it’s the best!
Captain Frosty’s has my favorite seafood. I don’t eat fried food but when I do, you an find me at Frosty’s, munching on clam fritters and sucking down an Orange Freeze (the yummiest, creamsicle concoction – I can’t go home without getting one!)
Kender & Sisters just opened up a few years ago and they have the best wood fired pizzas! Also the pulled pork sandwich is insanely good. My dad is obsessed and he knows his food.
My parents sold their restaurant, The Red Pheasant! It recently opened up under new management as Pheasant (by a sweet couple in their thirties) and the food is fantastic. They’re doing a farm to table concept and the cocktail list is incredible. I love the brick chicken and the clam pasta.
Inaho is our favorite favorite spot for sushi. Everything there is so so good. Like, so good. The scallop sashimi is fantastic.
Encore is the new restaurant at The Cape Playhouse (a great spot to see a show!) The food is very good.
Grill 43 is my one of my parents’ favorite restaurants – it’s the old Abici and looks very good.
The Seagrill is our favorite place to eat right now, but for something fancy (and usually we are pretty casual when I’m home). If you’re looking for a fancy night out this is the place to go. Everything is amazing.
What to do!
If I had my way, I’d just stay in the hammock all day when I’m home, but trips to Chatham and Orleans are also really fun.
If you head to Chatham, go to the lighthouse, and take a stroll on the beach. Lunch at the Chatham Squire is a must (think beer, oysters, and more seafood) or if you are feeling a bit more fancy, go to the Chatham Bars Inn. (The Chatham Bars Inn is one of the nicest hotels on the Cape too… chances are, you know someone who has gotten married there.) I love shopping along the main street. Midsummer Nights is one of my favorite little stores (they stock a bunch of my favorite designers like DVF + Tory Burch) but also the most gorgeous stuff for home (I love their candles + bought all my Turkish bath towels there.) I also really love grabbing ice cream or buying some salt water taffy at the Chatham Candy Manor.
And if you go to Orleans, you have to get lunch at The Land Ho. Their clam chowder is so delicious and it’s just a really fun spot. My favorite vintage store (in the world… way better, and better prices than here in New York) is also in Orleans — every time I go, I end up with a new beaded handbag, pair of oversized clip on earrings, or fur stole. I buy all of my furs there (cheap!) and have gotten some really fun costume jewelry and coats there as well. They have an entire bridal shop too. On the way home, stop at the Hot Chocolate Sparrow. Seriously good coffee – and their chocolate covered oreos are insanely delicious.
Lastly, what to do at night! I love grabbing cocktails (and hitting the raw bar) at Chapin’s. They have a great outdoor space and it’s always low key + casual. Harvest Wine Bar in Dennis is really nice, too. Yummy appetizers + snacks and really great wine. They almost have live music (fun fact – my dad sometimes plays there with his band!) and it’s just a nice but chill place to hang out. For the longest time, there weren’t any good wine bars on the Cape so this spot really filled a (necessary!) void.
I also am a little bit obsessed with The Woodshed in Brewster. They almost always have great music playing, and it’s dive-y + fun. It’s where all the locals go. When I was younger I lived at The Improper Bostonian during the summer… live music and lots of dancing. I have a lot of great memories from the nights I spent there… but don’t really go back there anymore… I’m too old! 😉
I didn’t mention Provincetown because I don’t get out there a lot, but that is a really fun day trip… other than that, these are all my “spots” in one place!
Do you have any favorite spots? Leave ’em in the comments section!