Cape Ann is a magical place. Only about an hour north of Boston, you’ll find a beautiful array of beaches and towns that have their unique character and personality. Not stuffy like Cape Cod or Newport, yet clean and beautiful, the best way to describe Cape Ann is a natural beauty, relaxed, hard working, and alluring.
Cape Ann has a long history in the colonial America days, with England colonizing the cape in 1623 as a profitable fishing town. Between the rich forest and sea resources, the Cape Ann towns grew and it became one of the largest commercial harbors for fishing and trade. The maritime towns and history still remain, with endless museums, colonial houses, and tidbits of history. The cape also has lighthouses and an array of estates.
Each town has its own vibe, attractions, and personality. We went to all 4 (either driving or stopping for the day), though we stayed in Rockport for the whole time. I wanted to give a brief run down of each, and suggestions that I have, then I have a full review and guide of Rockport coming your way later this week!
Rockport
Rockport is the dreamiest, quaintest beach town with what you would expect from a cape in Massachusetts. With gorgeous, wooden beach houses, Bearskin Neck (an idyllic town to eat and shop), and perfect, less crowded beaches, it leaves little to want. We stayed there for a week, and I have so many great things to share about the place in my comprehensive Rockport Travel Guide!
Gloucester
A much more rugged and industrial town, Gloucester is full of fishing companies, adding some grit to the New England charm. There’s plenty of fun bars, restaurants, and waterfront joys to experience. This is the largest, most bustling town of the cape, and is a good place to go for a beautiful beach, like Wingaersheek, or a fun night out at restaurants like Cape Ann Brewing Co.
Manchester-by-the-Sea
Another gorgeous beach town, the town portion is much more reserved yet quaint. There’s some really great clothing boutiques to shop at, as well as some adorable looking restaurants to try. We drove by Singing Beach, a unique beach that sings when you walk on the sand (and it is just as lovely as you’d imagine), but it’s currently closed to non residents. This is a great town togo to for lunch, shopping, and a bit of vitamin sea.
Essex
A bit more inland, Essex is the coolest river town! There’s riverside restaurants with extensive outdoor seating and views, a brewery, boutique wine and beer shop, and more antique stores than I could keep track of. It was probably my second favorite spot after Rockport, and would love to take a trip through to grab some antiques!
Cape Ann is a place I’d love to revisit, and would even consider owning property in during the future. With the elements of charm, small town vibes, and beauty, the small town beach feel is the best way to relax. This was exactly what I needed during covid. Stay tuned for more detailed posts about my stay!
All thoughts and opinions are my own.