June 7, 2025
Chatham, MA
Erin & Kyle
Things To Do
Lighthouse Beach
30 Main Street, Chatham, MA 02633
Considered the iconic landmark of the town, Chatham Light overlooks the infamous Chatham sand bars. Take a walk along the beautiful, sandy beach.
The Loop
Main Street, Chatham, MA 02633
The best 3.1 mile walk, run or bike in Chatham! You'll pass by some of the best places in town including Lighthouse Beach, Oyster Pond, Main Street and Shore Road.
The Squire
488 Main Street, Chatham, MA 02633
Grab a drink on the bar side at the Chatham Squire. With its roots tracing back to 1968, the Chatham Squire exudes a timeless charm that captures the essence of Cape Cod.
Chatham Cookware
524 Main Street, Chatham, MA 02633
Best coffee, pastries and Bacon, Egg and Cheese on a Portuguese Roll in town!
The Corner Store
1403 Old Queen Anne Road, Chatham, MA 02633
The best spot in town for a burrito, especially the day after a night at the Squire. Their breakfast burritos are top tier.
For all the days along the way