Chatham, Massachusetts embodies New England beach vibes and has the quaintest main street. I grew up going to Chatham many summers with my family, and it definitely holds a special place in my heart. Lighthouse Beach has gorgeous vistas, while Hardings Beach has gentler surf and warmer water since it faces Nantucket Sound.
MY favorite spots in town include the Candy Manor (I love the chocolate-covered cranberries), Violet's for boutique shopping, and Yellow Umbrella Books. Chatham Cookware supplies great grab-and-go breakfasts and lunches, and Monomoy Coffee Company will sort out your caffeine fix. I love their mochas and iced coffee, with bonus points for frozen coffee ice cubes that don't water down your drink.
The Squire is cozy spot for dinner or casual drinks, and the front porch of the iconic Chatham Bars Inn is perfect for a romantic cocktail. My grandmother spent a summer working at CBI, and our family celebrated my grandparents' 50th and 60th anniversaries there too. No trip to Chatham is complete without ice cream, and I heartily recommend Buffy's and Emack & Bolio's. My family once had a spirited 45-minute debate over which ice cream is better, but it's really a draw because they're both great! Don't miss any of the Oreo flavors at Buffy's, or the Serious Chocolate Addiction at Emack & Bolio's.
If you head to Chatham during the summer season, be sure to catch a Chatham Anglers baseball game. The Cape Cod Baseball League is a top collegiate summer league, and it's always fun to watch professional scouts checking out the players. Beachcomber Tours provides seal watching trips out of Chatham, and we had a memorable outing a few years back during which we saw literally hundreds of seals.
Lighthouse Beach gets its name from the Coast Guard station across the way. It's a quick drive or pleasant walk from town, but be warned that it has strong surf and no bathrooms on site. There have also been shark sightings in recent years (thanks to a large nearby population of seals).
Chatham Cookware serves up muffins, breakfast sandwiches, and gourmet deli sandwiches. It has a shady deck out back that is my favorite lunch spot in town.
The legendary Chatham Squire is a bar on one side and a restaurant on the other. It's dark, cozy, and tavern-like, and it serves my favorite clam chowder in Chatham.
Coconut Oreo ice cream from Buffy's. Coffee Oreo is also a favorite.
Old shingles meet new at the fish market. You can watch the commercial fishing boats come in and drop off their hauls and then pick up the freshest fish to take home and cook (or fish and chips for eating right on the pier).