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Day Trip to Chatham, MA – Cape Cod

June 2024

Day Trip to Chatham, MA – Cape Cod

Today we were exploring the Lower Cape and with a loose itinerary, we took our time getting ready before driving to our first destination, Chatham. Chatham is another well established town in Cape Cod that boasts beautiful homes, a lively downtown, fresh seafood, and plenty of beaches. 

Our first stop was outside of downtown at a popular breakfast spot with a unique view. Hangar B Eatery overlooks the Chatham Airport and if you are lucky, you can watch planes take off and land.

Read the dining review for Hangar B Eatery here!

Just a few minutes drive from breakfast and we were in downtown Chatham. With the morning already off and running, we were lucky to snag public parking in one of the lots behind the stores on Main Street. The downtown is very picturesque like it is out of a movie set. While I was eager to walk up and down Main Street, our first order of business was checking out the Chatham Pier Fish Market. 

It is a beautiful walk so I encourage you to walk when you are visiting. We walked through the neighborhood and simply enjoyed looking at the houses, each with a whimsy of beachside life. After a short walk, the road led to the ocean where the houses grew in grandeur. At the corner was the Chatham Bar Inn which is the ultimate luxury stay in Chatham. This five star hotel has the premier location overseeing the ocean with a private entrance directly to the beach. Fancy chartering a boat to Nantucket? The world is your oyster at Chatham Bar Inn.  We spied on all the people enjoying their breakfast outside in the gazebo guessing how much they must have paid to experience such luxury. And the private homes – sorry estates – in this area were just equally stately. There was no denying this part of Cape Cod is manicured perfectly and a prime spot for summer living. 

We arrived at the Chatham Pier Fish Market and took a walk up to the pier deck to see the view. While the fog was still around, it lifted enough to see some of the surrounding area. Seals and seagulls are frequent flyers here when the fishing boats come in the afternoon so if spotting them is on your list, visit Chatham Pier Fish Market in the afternoon. 

The market itself is a small stand off to the side with a window for takeout and a door for the fish market. Upon walking into the fish market, I expected it to be bigger than it was but it was certainly fresh. Even though we were full, it was so cold that a bowl of chowder certainly sounded nice.  But by the register, a daily special list indicated soft shell crab sandwiches were available for a limited time – and I have quite a soft spot for soft shell crabs. Not even hungry, we ordered it and shared the soft shell crab leaving most of the sandwich behind for lack for stomach space – and it was delicious.

We walked back to the downtown to start our exploration of all the shops. This seaside town features many fun stores that feature beach decor, Cape Cod labeled clothing, and lots of specialty shops. Our favorite stops included Where the Sidewalk Ends Bookstore, Chatham Candy Manor, Snowy Owl Coffee Espresso Bar, Demos Antiques, The Black Dog General Store, , Yellow Umbrella Books,  Ducks in the Window, among others. 

At the end of our walk we reached Chatham Squire – a very popular hang out pub that was very crowded. But our attention was focused on newly opened Aplaya – a Filipino tiki bar. This location turned the outdoor space into a tropical getaway complete with a full tiki bar, straw umbrellas, fun glassware, and great music. The vibe here is fantastic. During our visit, the place was bopping but we grabbed the last seats at the bar. We each ordered a beverage – pina colada for me (one of the best I have had) and margarita for Kevin, and the glassware was on point. The menu was primarily full of spicy food and I could tell the servers’ definition of spicy and mine were not the same. We went with the pork belly tacos which were super flavorful and delicious but 100% spicy. The pina colada came in handy to wash away the spice! Aplaya will certainly be the place to visit in Chatham. 

We returned to the car and drove to our final stop of our visit to Chatham – Chatham Lighthouse and Lighthouse Beach. Established in 1808 and currently operated by the US Coast Guard, t.his lighthouse is one of the few in the country that still operates 24/7. The beach here is beautiful and I can see this being a great way to spend the day in Chatham.

I was not sure how much there was to do in Chatham to fill the time but our day was a great showcase of what there is to do. You can easily spend the entire weekend or longer in Chatham alone and I can definitely see us returning here in the future. What a wonderful place to visit in Cape Cod!

Continue reading about our trip to the Cape Cod here!

Read all blog posts for Cape Cod here!

See our complete itinerary here!

Planning your own trip? Read the Perfect Itinerary for Cape Cod here!

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