24 Hours in Gloucester, MA

Having spent four years on the North Shore of Massachusetts attending undergrad at Endicott College, I realize now that I tended to take its beauty for granted. The turquoise blue and steel grey ocean waters, the rusty brown sands lining coastal beaches, and the ominous rock formations jutting into the sea are all reminiscent of the west coast’s beauty (with harsher winters and smaller cliffs). My recent dog sitting job has us heading this direction every weekend and we’re making the most of this location by planning some day trips. This past weekend allowed us to visit the town of Gloucester, a small coastal town known for its blue collar fishing industry, stunning beaches, and eclectic townies.

Since neither of us would touch this area with a 10-foot pole during the summer months due to overcrowding, we’re making the most of the off-season. The same shops, restaurants, and charm exist year-round, and we are both believers in Van Gogh’s saying, “If you truly love Nature, you will find beauty everywhere,” despite the temperatures, winds, or precipitation.

Gloucester has it all — delicious eateries featuring some of the freshest seafood around, antique stores and record shops, a brewery, and breathtaking views. We highly recommend heading this way if you’re in Boston for a visit. It’s a quick 45 minute drive from the city (traffic permitting) and feels like a different world in the best way possible. Check out how we spent a day in Gloucester, Massachusetts.

24 Hours in Gloucester, MA

Key Pointers

Since this town is on the water, be prepared for winds and dress for layers. Trust us when we say it’s better to be able to take layers off than not be able to put some on.
Wear comfortable shoes for walking around downtown and by the beach. If it’s a really nice day, you’ll want to walk all over the town.
Talk to the locals! Waiting for a table at a crowded restaurant? Poking around local shops? Window shopping? Chat with the locals, most shop owners and waiters/bartenders are friendly and they will more than likely have some great tips of what is worth your time while in the area.

Where to eat, drink, and be merry:

Cape Ann Brewing Company: Located right in Gloucester Harbor, this brewery is a town favorite. With their own exclusive brews and killer comfort foods, this place is one that you could sit in all day. Be sure to pick up a growler of your favorite lager to enjoy after your visit has come to an end.
Latitude 43: Though this establishment was being renovated during our visit, this is definitely one to check out. With some of the freshest sushi and the best deck right on the boardwalk, you’ll feel like you have a little piece of heaven for a while.

What to do:

Window Shop in Downtown Gloucester: With some of the cutest shops in the most diverse buildings, this activity can keep you occupied for hours. Some of our favorites were The Brass Monkey, Mystery Train Records, Bananas, and The Bookstore.
Visit the Fishermen’s Memorial: Located on Stacy Boulevard since 1925, this statue commemorates the estimated 10,000 fishermen’s lives who were lost at sea. The man at the wheel is made out of bronze and is watching over the men who risk their lives catching some of the regions most delicious meals.
Good Harbor Beach: Twin lighthouses to the left and stunning cliff side homes on the right, this place encapsulates the look and feel of North Shore towns. We walked along the soft sands for almost two hours taking in the dunes, rocks, and rough waters. This place is a must, no matter the time of year.