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Gloucester .

Gloucester is home to the country’s oldest art colony on Rocky Neck, with dozens of art galleries and the Rocky Neck Cultural Center. In fact, the Massachusetts Cultural Council has designated two distinct cultural districts within Gloucester— Rocky Neck and Harbortown, which is located near the city’s center. America’s oldest seaport, Gloucester has a rich maritime heritage of seafaring and fishing, a stunning harbor, unique restaurants and shops, and glorious white-sand beaches – qualities that have attracted artists for generations. The heart of Gloucester is still its working waterfront, which borders a busy downtown scene. Along Rogers Street, which hugs the shoreline, you will see fishermen, whale-watchers, fishing charters, schooner ships, pleasure boats and kayakers heading out to sea. Main Street is full of art galleries, eclectic boutiques, antique shops, and great restaurants, featuring the freshest fish and local farm fare. Many enjoy Gloucester’s free self-guided HarborWalk tour will take you through 42 stories that document the community’s history and its current culture.

Rockport .

With its uncommon magical light, breathtaking sunrises and sunsets, Rockport has been attracting notable painters and sculptors since the mid-1800’s. One of the oldest art colonies in America, Rockport presents the work of more than 300 artists at the Rockport Art Association and Museum and in over 30 galleries. Rockport is also home to the iconic Motif No. 1, reputed to be the most photographed and painted building in the United States, if not the world. A walker’s paradise, Rockport has public footpaths along the ocean, trails through the easily accessible Headlands, and a lively downtown with classic New England architecture. Visitors from all over the world come to enjoy the town’s New England seaside charm. They often exploring the unique galleries, shops and restaurants along eclectic Bearskin Neck –many housed in repurposed fishing shacks. Others traverse the jetty with views of the Straitsmouth Island lighthouse and Rockport’s vast seascape.

Machester-by-the-Sea .

Manchester-by-the-Sea (MBTS) is one of Cape Ann’s hidden treasures. Though it is small (population ~5,000) — MBST offers picturesque parks, beautiful beaches, and miles of conservation trails for hiking or biking. Those who love the outdoors can try paddle boarding in the Harbor or relax in Masconomo Park, a charming waterfront recreational area. Beachgoers head to Singing Beach, named for the sound the sand makes underfoot, which is walking distance from the town’s commuter rail stop, making it – and all of MBST— easily accessible from Boston. Nearly every business is locally owned, giving MBST a real “small town” feel. Almost all downtown establishments are open year-round; with locals and visitors continuing to frequent their favorite restaurants and shops long after the rush of the summer tourist season has ended. Within walking distance from the train are high-end consignment stores, vintage furniture shops, art galleries and historical houses. Manchester offers a selection of restaurants, where diners can enjoy a classic New England lobster roll or chowda, a gourmet French meal, or a sandwich to take to the beach or on a hike.

Essex .

Essex’s river basin with its tidal marshes offers a unique landscape with several restaurants situated on the shoreline. Live music and waterfront deck dining provide a casual backdrop for diners as they savor the moment and watch the tide ebb and flow, the clammers head back in or as the kayakers head out. Known as “America’s Antique Capital” Essex antique shops include Mid-Century Modern, Arts & Crafts style, Asian, American, European and Victorian period pieces, plus an assortment of “attic treasures.” Essex is graced with two outstanding museums; the Essex Shipbuilding Museum tells the story of how Essex became a major producer of the American Fishing Schooner. The town’s other museum, Cogswell’s Grant, is an 18th century farmhouse overlooking the Essex River was the summer home of collectors Bertram and Nina Fletcher Little. Cogswell Grant now houses the couple’s celebrated collection of American folk art. On the water, you can head “down river” via paddleboard or kayak, or on boat cruise or fishing excursion. Back on land, there are miles of conservation woodlands to hike or mountain bike along the nature trails.