Things To Do
Here are a few of our favorite spots in the area for you to check out.
Main Street
Main Street, Chatham, MA
A lively street with shops, restaurants, bars, and lots of Cape Cod charm.
Chatham Squire
487 Main Street, Chatham, MA 02633
A must go to. Super fun and classic Cape Cod dive bar any time of day!
Chatham Lighthouse
37 Main Street, Chatham, MA 02633
Historic landmark with scenic coastline views.
Chatham Pier Fish Market
45 Barcliff Avenue, Chatham, MA 02633
The best local spot for your lobster roll fix.
Bayview Terrace at Chatham Bars Inn
297 Shore Road, Chatham, MA 02633
Hands down the best spot for drinks with a view! Nothing beats having a cocktail in the adirondack chairs.
Nauset Beach
250 Beach Road, Orleans, MA 02653
Our go to beach! And where Sean proposed in March 2025. Note: parking is $32.50/day and is credit card only.
Hog Island Beer Co.
28 West Road, Orleans, MA 02653
If you're looking for local craft beers, this is your spot.
The Captains Golf Course
1000 Freemans Way, Brewster, MA 02631
A great public golf course where we get a lot of rounds in during the summer.
For all the days along the way