Cape Ann Plein Air Festival Week 2021!

Cape Ann Plein Air Festival Week 2021 is underway! 35 artists from across the country have landed here in town and will begin painting.
Find out why artists from around the world are drawn to America’s oldest sea port. Stroll through artist galleries and studios nestled on the Atlantic. Grab lunch on the water overlooking a working fishing harbor. Experience arts and culture at one of the world-class museums, theater, or heritage center. Venues offer a calendar of special events and daytime galleries perfect for a casual visit or an overnight stay.
Many paintings will be available for sale during the full duration of the competition and festival. Selected works will be shown and available for sale during the Gala Reception and Awards Presentation, at the conclusion of the competition. This is your chance to purchase works by some of the top names in contemporary painting.
For more information visit:

Fall in Love With Autumn on Cape Ann


Autumn is gorgeous in the Cape Ann Region and ideal for wood land hikes and seaside walks on Greater Cape Ann’s numerous trails and pathways for a drive along the Essex Coastal Scenic Byway. Book a long weekend to enjoy the spectacular fall colors, Cape Ann Plein Air, Rockport Harvestfest, Essex Clamfest, and even some Haunted Halloween Happenings

Take A Tour Through Cape Ann History

Echoes of the past are hidden around every corner of Cape Ann, and visitors can explore the region’s hundreds of historic homes, grand monuments and businesses–all with centuries of tales to tell. If you’re in Gloucester, take a stroll on the self-guided HarborWalk to see many historical sites and then continue to Stacy Boulevard for a moment with the Gloucester Fisherman. A stone’s throw from Stacy Boulevard is Cape Pond Ice, established in 1848, and still providing tons of ice to the fishing fleet daily. In Rockport, tour historic downtown along main street and pass by some of the first homes built by English settlers in the 18th century. For a taste of colonial New England, visit Essex’s Cogswell’s Grant to discover a restored 1728 farmhouse containing a collection of American folk art or explore early American cemeteries and examples of 17th century vernacular architecture in Manchester and Ipswich. Learn more about the region’s history by visiting

Relax, Restore and Revitalize

Whether solo or with a friend, spend a day recharging your body and mind. Pack a picnic from Common Crow Natural Marketplace or Seaview Farm. Bring your yoga mat, favorite book or journal and exhale in one of Greater Cape Ann’s many serene locations. You may drawn to the idyllic Dog Bar Breakwater at Eastern Point Lighthouse in Gloucester, Masconomo Park & Tuck’s Point in Manchester-by-the-Sea, Back Beach in Rockport, the Stavros Reservation in Essex, or the Iconic Crane Estate in Ipswich. If you would rather meditate indoors, find your Zen at Treetop Yoga, Saltwater Massage Studio or Soft Touch Salon. Treat yourself to a day of revitalization in the Greater Cape Ann region.

Go For A Hike

Feed your body, mind and soul simply by putting one-foot in front of the other and exploring one of Greater Cape Ann’s many scenic trails. If you’re in Rockport, pack your knapsack and head on over to Halibut State Park. Essex Features the Millstone Hill Conservation Area, Cox Reservation and Cogswell’s Grant; Manchester-by-the-Sea, the Agassiz Rock Trail and Coolidge Reservation. Local favorites in Gloucester are Ravenswood Park and Dogtown Common (where Gloucester was originally settled). Ipswich is home to Appleton Farms, Willowdale State Forest and Strawberry Hill. These trails all offer beautiful vistas, trails for all abilities and ample opportunities to get away from it all and appreciate the Greater Cape Ann region’s natural beauty.

Attend a Performance or Festival

A visit to Cape Ann is only complete by experiencing live music at a local restaurant or nightspot; watching a dance performance, concert or play; attending one of Cape Ann’s renowned community events and festivals, including St. Peter’s Fiesta, Waterfront and schooner festivals in Gloucester, the Essex Clamfest, Harvest Festival in Rockport, Manchester’s Festival by the Sea and, of course, the winter holidays-Celebrated in all four communities, each with their own special flourishes. Whether it’s the height of summer or the heart of winter, there is always a performance, event, or festival happening. Visit the community calendar of events at