Seek • October 1, 2024

Experience Chatham, Massachusetts

72 Hours in Chatham, Massachusetts

Chatham, Massachusetts is a very special place for me and my family. We have been going with friends for over 30 years. First as young, single coeds leaving New York for the weekend, then adding in kids. Our last visit this July included 8 parents and 13 kids - can you say outnumbered?! While you can go to Cape Cod and visit many beautiful towns or even hop on a ferry to the gorgeous surrounding islands, this is just a guide to Chatham. Chatham is a pretty large area surrounded by several beaches and a long Main Street filled with shops and restaurants. So you can definitely fill your days with fun and sun! While you are strolling, be sure to take in all of the beautiful hydrangeas and quintessential Cape Cod shingle homes.

O’So Pro Tip:

Traffic is heaviest on Saturdays, try to avoid arriving or leaving that day. Even better, visit in September or October, while it’s still beautiful but less expensive and crowded. 

Where to Stay:

Wayside Inn - Traditional rooms on Main Street 

Chatham Bars Inn - Exclusive resort on the water 

Greyfinch Chatham Inn - Outside of town, but close enough If you plan to stay for more than a few days.

Rent a house - there are also some good rental companies (Pretty Picky Properties) or vrbo and airbnb options.  Many only rent for a minimum of a one week stay, but I’ve noticed more properties are becoming available for shorter stays

Where to Play: 

Lighthouse Beach 

Ridgevale Beach 

Oyster Pond 

Chatham A’s game 

Drive along Shore Road and take in all the beautiful scenery

Where to Eat and Drink: 

Breakfast/Lunch:

Chatham Cookware

Monomoy Coffee

Chatham Cheese Company

The Red Nun

Dinner:

Impudent Oyster

Wild Goose Tavern

Chatham Bars Inn (beach house grill)

Pisces Coastal Kitchen

Bluefins Sushi and Sake

If you’re staying at a house, consider a trip to Chatham Fish & Lobster or Chatham Pier Fish Market for the freshest fish and lobster!

Drink:

The Squire

Chatham Bars Inn (on the Veranda or Beach Lawn)

The Red Nun

Where to Shop: 

You will want to wander in all the shops on Main Street, but here are a few faves:

White Marlie

The Fisherman’s Daughter

Lola Mer

The Squire Shop

Mahi Gold

Candy Manor