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Things To Do

Main Street

Main Street, Chatham, MA

Plenty of cute shops, bars and restaurants available to stop in should you have some additional time while visiting Cape Cod for the weekend!

Harwich Port

Harwich, MA

Harwich Port also offers a lot of great shopping as you are exploring the area!

Chatham Squire

487 Main Street, Chatham, MA 02633

A Chatham staple! Great spot on the Main Street for lunch, a drink, or even live music in the evenings!

Chatham Bars Inn

297 Shore Road, Chatham, MA 02633

Beautiful hotel in Chatham with great views! Either walk around, see some hydranges, or have a meal at one of their many spots. Rumor has it you used to be able to catch Dan "Noodles" Peek working in the kitchen here!

Impudent Oyster

15 Chatham Bars Avenue, Chatham, MA 02633

A great, local spot for just a drink or even dinner if you're interested! Similar to CBI, the Impudent Oyster was a former favorite of a Peek family member or 2.

Chatham Pier Fish Market

45 Barcliff Avenue, Chatham, MA 02633

One of the best lobster rolls you can get in the Cape! But this is definitely a stop by, and pick up place - do not expect a lot of available seating. When it is warm enough, you should even be able to see seals in the water at the Pier - but we fear you likely will not see them in October.

Sesuit Harbor Cafe

357 Sesuit Neck Road, Dennis, MA 02638

Another top tier location for a lobster roll and views! During the off-season months, they are only open until 2:30pm so this could be a great spot for lunch in Dennis. Should the weather be warm enough, grab a lobster roll, sit at the Picnic tables on the water, and a beverage of your choice (BYOB). Also a beautiful area to drive around!

Marion's Pie Shop

2022 Main Street, Chatham, MA 02633

A great little bakery close to Harwich. Just be careful of their hours - but they at the very least offer a GREAT cinnamon roll.

Sundae School

606 Main Street, Harwich, MA 02646

Although it may be a bit chillier this time of year, you can't come to the Cape and not get some ice cream. Sundae School is one of the Cape's more renowned ice cream spots - so why not give it a try!

Lighthouse Beach

30 Main Street, Chatham, MA 02633

When driving around Chatham, you can find some beautiful houses in this area and the view down from Lighthouse Beach is breathtaking whether you want to just stop for the views or take a walk down (weather permitting).