Before moving to Boston, I had no idea what Cape Cod was, let alone what it offered those looking for the perfect summer escape. So when my friends first asked me to join them for a weekend down the Cape, I naively hopped in their car and asked how long till we hit the town of Cape Cod. To my pleasant surprise, I quickly found out that Cape Cod is not just a single beach city, but an entire peninsula comprised of fifteen unique towns.

To many East Coasters (and what it eventually became to me), the Cape is the quintessential New England summer getaway filled with biking, sailing, whale watching, and best of all…seafood eating and margarita drinking. Over the past four years, I’ve visited Cape Cod a handful of times, exploring the various towns and discovering what a number of them have to offer those looking for the perfect summer getaway. Through all my Cape travels, I’ve come to recognize that my absolute favorite Cape Cod destination is Chatham, MA.

WELCOME TO CHATHAM!

Located on the elbow of Cape Cod, Chatham is a picturesque seaside town known for its charming cottages, sandy beaches and breathtaking coastal scenery. Unlike some of the other Cape towns, Chatham offers its visitors plenty of activities to fill their days. The main street is lined with dozens of boutiques and restaurants, and the nightlife is recognized as the some of the best in the Cape. Because there is so much to do, Chatham is the perfect town for a group of friends, couples or families to visit. If you’re lucky enough to find yourself in Chatham, take a look at my recommendations below so you can make the most out of your trip.

Chatham MA 02633 Cape Cod Houses
Chatham MA 02633 Chatham Fish Pier
WHAT TO DO:
  • Bike around town to the Chatham Lighthouse and Monomoy National Wildlife Refuge.
  • Go shopping on Main St.  •  The shops in Chatham offer more than just beachy knick knacks and souvenirs — there are plenty of options ranging from chic boutiques to casual clothiers, to home decor stores and unique gifts shops. My favorites include Fisherman’s Daughter and The Mayflower.
  • Hit the beach! Chatham Lighthouse Beach is recognized as one of the most beautiful beaches in the Cape, but it has strong tides so pay attention to warning signs. For those looking to spend a day in the water, check out Hardings Beach just around the bend.
  • When you visit Cape Cod, getting on the water is a must! There are a number of boating companies in the area that offer a variety of tours and cruises. ⇢ Check out the seal watch cruise from Beachcomber Boat Tours or one of the many cruise options provided by the Chatham Bars Inn Private Fleet.
WHERE TO EAT & DRINK:
  • Chatham Cookware  •  Quaint cafe to grab a quick breakfast or lunch. ⇢ Must try the French Breakfast Muffin or the Spinnaker Sandwich.
  • Chatham Fish Pier Market  •  Fresh seafood to-go with amazing water views.
  • Kream N’ Kone  •  Casual counter-serve restaurant with a huge menu full of seafood and burger options.
  • Bluefins Tuna & Sake Bar  •  Amazing restaurant for fresh sushi and seafood lovers!
  • The Squire!  •  The Chatham Squire is a classic Cape bar and the most popular on the peninsula. Grabbing food/drinks at The Squire is a must do when you’re down the Cape. The place has a vibrant atmosphere and great energy. *The Squire is so popular that a line wraps around the building virtually ever night in the summer — get there early to avoid the wait!
  • Beach House Grill at Chatham Bars Inn  •  This is my favorite spot to relax and grab a drink in Chatham! While it’s on the pricier side, the stunning water views and daily live music (from 12-4pm) make it an unforgettable experience. ⇢ My go-to drink is the Salted Watermelon Margarita. *More to come on Chatham Bars Inn below!
WHERE TO STAY: CHATHAM BARS INN

The Cape is all about sandy beaches and salty oceans. So when you’re looking to vacation in classic Cape Cod fashion, being steps away from the water is a must. Chatham Bars Inn is a spectacular 25-acre oceanfront resort that embodies the idyllic Cape Cod experience. The grand lobby, plush rooms, luxurious amenities and array of gourmet dining options transport you into a world of relaxation and indulgence, making you wish everyday could be like this. Situated steps from the beach, the boardwalk calls you to the ocean with private beach cabanas, fat-tire bike rentals, beach yoga, and sunset bonfires. Looking for a break from the sand? The heated outdoor pool is also a great place to lounge in the sun and check out the resort’s very own Vineyard Vines pop-up shop.

And let’s not forget about the food! You can enjoy gorgeous panoramic ocean views while eating dinner at STARS, the hotel’s fine dining restaurant; or for a more casual experience, enjoy seafood and burgers at CBI’s upscale tavern, The Sacred Cod. Most notable of all – and where I recommend every visitor should check out regardless of where they stay –  is the Beach House Grill where you can grab a watermelon margarita and indulge in the hotel’s seaside clambake.

Though a stay at the Chatham Bars Inn is on the pricier side, especially during the peak summer season, the proximity to the water, 5-star service, deluxe amenities, and classic New England atmosphere makes your stay an unforgettable experience in it of itself.

*Not sponsored
Chatham MA 02633 Chatham Bars Inn
Chatham MA 02633 Vineyard Vines Chatham Bars Inn
OTHER MUST HAVE CAPE COD EXPERIENCES:
  • Provincetown: Check out (1) the Aqua Bar for drinks and an amazing view of Cape Cod Bay, and (2) the Lobster Pot for one of the best lobster rolls in New England. You can also take a fun off-roading tour of the sand dunes or set sail on a whale watching cruise. 
  • Wellfleet: Beachcomber
  • Harwich: Wequassett Resort & Golf Club ⇢ Grab a drink and enjoy the scenery at the Outer Bar & Grill
  • Dennis: Devil’s Purse Brewery
  • Check out one of the Cape League baseball games in any town!