How to Have an Epic Weekend in Cape Cod

A Perfect Weekend Itinerary for Cape Cod



B and I lived on the Cape for two summers while performing at a summer stock theatre in Falmouth (Upper Cape). Those were some of the best summers of our lives, and we got to explore most of the Cape whenever we weren’t rehearsing. From a former, seasonal local, here’s some of the best of the best in Cape Cod. On return visits, we typically found a spot to stay near the Bourne Bridge (Falmouth or Woods Hole), so a lot of these dinner recommendations are closer to that area of the Cape. So without further ado, here’s your perfect weekend in Cape Cod.

Friday Night

Cape Cod is a quick drive from NYC, Boston or Vermont, so we typically head out in the afternoon after work and get there by dinner. B and I have camped at the Sippiwisset camp sites, but as of 2019, they are closed. I looked up some AirBnBs and there are some great ones right around $100/night. For Cape Cod, this is a good deal. Depending on the season, it is not necessarily the cheapest weekend destination.

Okay, so you’ve made it to Cape Cod, and you’re looking for some fresh seafood for an early dinner. B and I LOVED the Raw Bar in Chatham(Lower Cape). If you can make it between 3:30-5, you’ll make it for happy hour for some half-priced, raw bar finds and drink specials. Downtown Chatham is also a sweet place to shop and hang out with a small beach to get your fix before settling down for an early night.

Saturday- Provincetown/National Seashore

Alright, it’s time to get up early and head to Provincetown! This eclectic, historical, seaside town is a must see if you’re in Cape Cod. When we went to Provincetown, we parked at the Pilgrim Museum. There was a deal for free parking if you paid for museum admission. That’s a win-win for us! Since you’re going to pay to park anywhere you go, this is a no-brainer. The Pilgrim Museum is home to a monument that marks the spot where the Mayflower first docked in the “New World” before moving on to Plymouth Rock where they settled. You can walk up to the top and get the best view in all of Provincetown. Keep in mind, it’s quite a walk to the top and there are no shortcuts. When B and I went, it was POURING rain so the view was obstructed, but it was still worth it.

The walk to the top of the Pilgrim Museum Monument!

After walking up the monument and perusing the rest of the pilgrim museum, B and I headed downtown. There is plenty to see and do in this city, so you will not be disappointed. After lunch at Tin Pan Alley, we decided to wrap it up and head back down the Cape. You could honestly spend an entire vacation exploring the nooks and crannies of Provincetown, it’s an incredible city. But, we only have a weekend, and it’s time to move on!

After your morning/afternoon in Provincetown, head to the National Seashore to take in the beach. There are five, main beaches on the National Seashore from Provincetown to Chatham and it’ll cost you about $20 to park at one. We’ve probably visited every one of them at different times and they are all incredible. Check out the National Seashore website and pick the one that fits your needs the best (I’ve added a couple of photos of different ones for some inspiration). After spending time at the beach, pack up the gang and head back home. If you’re staying in upper Cape Cod, check out Anejo Mexican Bistro and get some margaritas to cap off your night. They are INCREDIBLE there. You’ll thank me later. 

Sunday 

Sundays are for late mornings, mimosas and bike rides. So start yours off at the Pickle Jar for some breakfast. I personally like the Pastrami and Kale Hash, but it’s all amazing. You can explore the Falmouth downtown, but it’ll be pretty sleepy on a Sunday morning. After this, hop on your bike and take the scenic bike path from Falmouth to Woods Hole.

**If you’re staying on another part of the cape, there are a ton of other bike paths, I just don’t have personal experience with them!

The trail is about 10 miles long (depending on where you start) but it’s easy going, with virtually no incline. Even the most novice of bike riders will be able to handle this one. As your reward, you will end up in Woods Hole, another adorable Cape Cod town. Woods Hole is the where the world famous oceanographic institute is (like the one in Jaws!), so there are a lot of opportunities to learn about local wildlife, including boat tours and an aquarium. We love all things aquarium so that’s a must for us!

Scenic Bike Path in our Weekend in Cape Cod

After Woods Hole, head back to Falmouth (remember: unless you have a one way rental, you’ll have to ride your bike back to Falmouth). If you’re looking for some more seafood, try the Quarterdeck in Falmouth or another favorite of ours is Osteria La Civetta, if you’re looking for some great Italian. Then, have a small “night cap” at Ben and Bill’s homemade ice cream. You’ll sleep well that night knowing you got the most out of Cape Cod in your epic weekend adventure.

Whew- so not that most relaxing beach vacation, but you definitely got the most out of your Cape Cod weekend. Have you visited Cape Cod? Did we miss any “must dos”? Leave your comment below and let me know!