Theresa & Brian
Things To Do
Main Street
Chatham is one of walkable towns on Cape Cod. It’s also one of the most endearing, combining a classic “Main Street” atmosphere with modern amenities and a wide variety of options for dining & shopping.
Chatham Squire
If you’re looking for an evening out on the town, you’ll probably find yourself enjoying last call at The Chatham Squire. The Squire features live music, food and drinks, as well as the latest closing time in town.
Sandwich Boardwalk
The iconic Sandwich Boardwalk, originally built in 1875, is one of the best places on Cape Cod to catch a sunset. It's one of Theresa's favorite places in her home town.
Sundae School Ice Cream
Sundae School opened its doors in 1976 and has been a Cape Cod go-to ever since. As their name suggests, they're known for their homemade ice cream sundaes.
Chatham Bars Inn
Go full relaxation mode in an Adirondack chair with sweeping views of Pleasant Bay and perfectly manicured gardens. Lots of choices for places to eat and drink, each one more beautiful than the last.
Visit the Islands
If you're staying a few extra days, Martha's Vineyard is a great day trip. Catch the ferry from Woods Hole to Vineyard Haven or Oak Bluffs. Nantucket is a longer adventure, catching the ferry from Hyannis. You can bring a car, hop on the bus, or rent a bike or moped to explore the islands.