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Hit the Road: a 40-mile getaway to Gloucester

Hit the road with the whole family + explore Gloucester. | Photo by @lukewallacetravels

Hit the road with the whole family + explore Gloucester. | Photo by @lukewallacetravels

Last month, we kicked off our summer road trip series, Hit the Road, with an outdoor adventure to Acadia National Park. If you checked it out, we’d love to hear about it.

This month, we’re continuing the series with a 40-mile trip to Gloucester for a quick getaway. From beautiful beaches to scrumptious seafood, this Cape Ann city offers a little bit of everything — making it the perfect end-of-summer vacay.

Before you start packing your bags, here’s everything you need to know about the area + our insider recommendations.

Drive time: ~50 minutes from downtown

Est. population: 30,291

Avg. high in July: 77°

🎟️ Things to do

Hammond Castle Museum, 80 Hesperus Ave.

This castle was built in 1926 because inventor John Hays Hammond, Jr. needed space for his vast array of ancient artifacts dating back to the Renaissance — take a guided or self-guided tour of the spacious castle with views of the Atlantic shore line.

Gloucester Harborwalk, 9 Dale Ave.

Step off at St. Peter’s Square or Fitz Henry Lane to find 42 granite posts that explore Gloucester’s harborfront and history. Pro tip: download the Harborwalk app on your phone for an interactive video to complete the experience.

Eastern Point Lighthouse

Located at the oldest Seaport in America, visit the harbor that’s supported fishermen, whalers + traders since 1616. Fun fact: “The Perfect Storm” was filmed around Gloucester and featured the historic lighthouse.

We highly recommend catching a sunset by Annisquam Lighthouse. | Photo by @robdaviesimages

We highly recommend catching a sunset by Annisquam Lighthouse. | Photo by @robdaviesimages

Annisquam Lighthouse

While there is no longer public access to the road leading up to this lighthouse, you can take in the views from Wingaersheek Beach (right across the Annisquam River).

Rocky Neck Art Colony, 6 Wonson St.

Take a walk on the artsy avenue full of work from painters, potters, textile designers, photographers + jewelry makers. Find a list of exhibitions here.

Go whale watching

The Cape Ann Whale Watch + 7 Seas Whale Watch take visitors to Stellwagen Bank, a national marine preserve ~12 miles off the coast of Gloucester.

Take a boat tour

If you prefer to explore Gloucester by boat without searching for whales, check out one of these Schooner and boat tours for some chill cruising.

Check out a festival

The infamous Greasy Pole contest may have passed, but Gloucester hosts other exciting programs. The Blues Festival (Sat., Aug. 13) and Waterfront Festival (Sat., Aug. 20-Sun., Aug. 21) are both coming up next month.

Visit a local beach

Good Harbor Beach and Stage Fork Park (home to Half Moon and Cressy’s beaches) are both located in Gloucester. We also recommend taking a quick drive over to Manchester-by-the-Sea to visit Singing Beach. Curious how the beautiful shore got its name? The sand makes a squeaky sound as you walk across it.

🍔 Grub to eat

Sugar Magnolias, 112 Main St.

Gloucester knows how to do brunch, which you can confirm for yourself by stopping at Sugar Magnolias. From omelets to a lobster taco, there’s something for everyone.

Passports, 110 Main St.

Located in the heart of Cape Ann, Passports is inspired by cuisines from all over the world. Think: paella, seafood casserole, and even a meatloaf tower.

DRIFT Cafe, 3 Main St.

Tradition meets modernity in this trendy space with coffee, cocktails, small plates + live music.

It doesn't get much more Massachusetts than Lobsta Land. | Photo by @trufflefriesandstuff

It doesn’t get much more Massachusetts than Lobsta Land. | Photo by @trufflefriesandstuff

Lobsta Land, 84 Causeway St.

Eat like a local and select from a menu of quality seafood dishes like spicy Littleneck clams and a crab cake sandwich.

Woodman’s, 119 Main St., Essex

A close drive from Gloucester, you’ll want to get the New England fried clams from this Essex seafood spot. Why? Woodman’s invented them back in 1916.

🏨 Overnight accommodations

If you get a wild hair and decide to turn this quick day trip into an overnighter, here are some spots to stay.

Ocean House Hotel, 107 Atlantic Rd.

Resting on the rocky shores of Cape Ann, this historic hotel has been housing guests for over 100 years. Enjoy a nautical stay with views of the Atlantic, luxury rooms + amenities like complimentary bikes.

Beauport Hotel, 55 Commercial St.

Just under 40 miles from Boston, you can stay in the oldest fishing port in America + enjoy coastal accommodations and soothing decor.

Cape Ann’s Marina Resort, 75 Essex Ave.

Whether it’s you or your boat that needs to retire for the night, this Marina Resort welcomes guests with beautiful ocean views, fantastic dining services + plenty of local activities.

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