Weekend travel

Weekend Road Trip in Cape Ann, Massachusetts

Weekend Road Trip in Cape Ann, Massachusetts

Celebrities, politicians and other celebrities have long flocked to Cape Cod for a summer seaside getaway. But a more relaxed coastal experience filled with similar scenery, historic architecture and activity awaits you about 100 miles north, the along the northern Massachusetts coast.

Cape Ann – “the other cape” as it is sometimes called – is the place to go when you want to relax on beautiful beaches, enjoy cultural experiences and taste great seafood, without the traffic wall to wall that afflicts Route 6 towards Cape La cod.

Find more weekend road trips: Coastal Rhode Island | Lower Adirondacks

How to get to Cape Ann

Driving from Albany to Cape Ann, via I-90 East to 95 North, takes just over three hours. Add about 40 minutes from Poughkeepsie and point south.

The Newburyport/Rockport line of the Massachusetts Bay Transportation Authority commuter rail runs from Boston to several points around Cape Ann. Since many small towns lack ride-sharing services, you will need to rent a car once you get there.

Day 1: A creaky beach, whale watching and the oldest artist colony in the country

After refueling with a breakfast burrito and cold brew at laughing seagull (4C Summer St., Manchester) head towards Singing range (121 Beach Street), the crown jewel of Manchester-by-the-Sea. Parking on the beach is for residents only in the summer, but the MBTA station, less than a mile away, offers free parking. (You’ll still pay a $10 tour fee, cash only.) This white-sand stunner gets its unique name because of the grains of sand that create a sound like sneakers scuffing a gym floor.

Singing Beach in Manchester-by-the-Sea takes its name from the creaking sound made when you walk on the sand.

Singing Beach in Manchester-by-the-Sea takes its name from the creaking sound made when you walk on the sand.

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Head north to Gloucester. The newly expanded maritime gloucester (23 port loop) puts the town’s fishing roots into context. Kids will enjoy the pocket aquarium, where pipefish, Jonah crabs and other sea creatures accidentally caught in fishing nets are given a temporary home until they can be safely released. Small but mighty, the Cape Ann Museum (27 Pleasant Street, Gloucester) hosts permanent and rotating exhibitions, including the work of luminist painters. New Cape Ann Museum Greenabout two miles away, focuses on contemporary work in an indoor/outdoor exhibition space.

Visitors can explore Gloucester's fishing roots at Maritime Gloucester, which has a child-friendly pocket aquarium that temporarily houses sea creatures accidentally caught in fishing nets.

Visitors can explore Gloucester’s fishing roots at Maritime Gloucester, which has a child-friendly pocket aquarium that temporarily houses sea creatures accidentally caught in fishing nets.

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from Gloucester Whale Watching of the 7 Seas (63 Rogers Street) and Cape Ann Whale Watch (415 Main Street) both offer exuberant, naturalistic tours where you’re guaranteed to spot one or more species of whale, as well as dozens of seabirds and the occasional dolphin, porpoise or shark.

Lunch and dinner options abound in the city. Try it Seaport Grid (6 Rowe Square) for stuffed lobster rolls and punchy cocktails, or Passports (110 Main Street) for tasty new American cuisine. Two Italian grocery stores, Virgil (29 Main Street) and Sclafani’s (49 Washington Street)serve specialty sandwiches with imported meats, cheeses and olive oil, as well as freshly baked pastries.

Good Harbor is one of Gloucester's most popular beaches - for good reason.

Good Harbor is one of Gloucester’s most popular beaches – for good reason.

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Gloucester’s beaches are beautiful but expensive: expect parking fees of $20-$30 (book online). good port receives the most traffic, while Wingaersheek, a winding stretch of sand, dunes and tidal flats, is a favorite with locals. Go kayaking, stand-up paddleboarding and surfing at Beach Pavilionbetween Gloucester’s famous “Man at the Wheel” sculpture, which commemorates fishermen lost at sea, and the great Hotel Beauport (55 Commercial Street).

Rocky Neck Art Colony (6 Wonson Street), a quintessential coastal community located a short drive from downtown, is the nation’s oldest continuously operating artists’ colony. Several galleries offer curated exhibitions. You can buy original pieces – from paintings to textiles and sculpture – in the colorful artist-run shops along the main street.

Rocky Neck Art Colony is the oldest continuously operating art colony in the United States.

Rocky Neck Art Colony is the oldest continuously operating art colony in the United States.

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Day 2: A mansion, a paper house and outdoor live performances

Start early along the Essex Scenic Coastal Drive at Ipswich. The town center has shops and cafes in repurposed historic buildings, as well as a small riverside promenade. For breakfast, the new relocation Sandpiper Bakery (29 Main Street North) makes hearty homemade quiches, breakfast sandwiches and pastries. Don’t miss the cardamom buns.

Off the wooded path of Argilla you will find Russell Orchards (143 Argilla Road, Ipswich), a serene 120-acre fruit farm. Depending on the month, you can pick your own blueberries, raspberries, currants, cherries and more. The farm also has an on-site bakery offering fresh cider donuts and other treats.

Perched on top of a hill, Castle Hill on the Crane Estate (290 Argilla Road, Ipswich) is a spectacular example of Stuart style architecture. Take a guided tour of the cupola for stunning 360-degree views of the marshes and ocean. Or stroll one of Castle Hill’s two beautiful beaches, the European-style gardens and the Grand Allé, a half-mile “ha ha” – landscape architecture’s version of an optical illusion, in which the end seems to fall into the ocean.

Castle Hill on the Crane Estate offers a great example of 17th century Stuart style architecture.

Castle Hill on the Crane Estate offers a great example of 17th century Stuart style architecture.

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At lunchtime, return to Essex. On the way, first eat the dessert at DownRiver Ice Cream (241 John Wise Ave), an unassuming roadside stand that offers over 30 flavors of creamy, dreamy treats. Or head straight for the most century-old savory Essex Woodman (119 Main Street), which has racked up dozens of awards for its fried fish platters and sandwiches. Elegant and rustic newcomer Great Marsh Brewing Company (99 Main Street) serves upscale pub fare like burgers and po’boys, plus nearly 20 beers.

Woodman's of Essex has racked up dozens of awards for its fried fish platters and sandwiches.

Woodman’s of Essex has racked up dozens of awards for its fried fish platters and sandwiches.

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Twenty minutes further up the peninsula in the village of Rockport you will find Bearskin collar, a former strategic outpost during the War of 1812, it is now a shopping district of small galleries and independent shops in traditional cobble-covered buildings. Many are touristy, but you can find some gems. It is also the home of Reason 1 (Bradley Wharf, Rockport)a photogenic scarlet fishing shack that some say is the most painted building in America.

Rockport claims its iconic fishing shack, Motif #1, is the most painted building in America.

Rockport claims its iconic fishing shack, Motif #1, is the most painted building in America.

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If you have half an hour to spare, go to paper house (52 Pigeon Hill Street). Its walls, furniture and even curtains were made from newsprint in the 1902s by the eccentric engineer Elis Stenman, who invented the paperclip-making machine.

For evening entertainment, the Shalin Liu Performance Center (37 Main Street), built in the style of elegant Victorian seaside mansions, is a superb acoustic venue for live music. The enchanting, off-the-beaten-track location of Windhover Center for the Performing Arts (257R Granite Street) is enhanced by its intimate outdoor performance space, which features live theater from Gloucester Stage.

The outdoor stage at the Windhover Center for the Performing Arts hosts outdoor performances throughout the summer.

The outdoor stage at the Windhover Center for the Performing Arts hosts outdoor performances throughout the summer.

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Where to sleep in Cap Ann

As with most New England coastal destinations, budget accommodations are hard to come by in Cape Ann. This relaxed condo in Ipswich, adjoining protected wetlands, is great value for a small group. For a single traveler or a couple, this base is just five minutes from downtown Essex. If you don’t mind sharing a bath, this cozy private room in Gloucester is conveniently located to many attractions.

The harbor inn (71 Western Avenue, Gloucester)close to a variety of Gloucester attractions, is an intimate, mid-priced delight, with an affable innkeeper serving pastries from around Cape Ann for breakfast.

For a boutique option, the Emerson’s Inn (1 Cathedral Ave, Rockport) is a comfortable hotel in a recently renovated historic coastal property. It offers some of the best views in all of Cape Ann, luxurious yet unpretentious decor, and exceptional hospitality.

The Emerson Inn is a cozy boutique located in a newly renovated historic coastal property.

The Emerson Inn is a cozy boutique located in a newly renovated historic coastal property.

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