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Fall Breaks: Labor Day Weekend and Beyond

Fall Breaks on Cape Ann - Labor Day and Beyond
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Things to Do on Cape Ann

There are many reasons to come to the North Shore for a fall vacation or getaway: from cooler breezes off the shore, less traffic in town and at the beaches, and a wide variety of great festivals, concerts and events. Not to mention, Atlantic Vacation Homes offers lower off-season rates starting in September. 

As you start planning your fall break, check out these fantastic events and festivals coming up in September and October. The fun doesn't stop just because the calendar marks the end of summer!

September Events on Cape Ann / North Shore 

Gloucester Block Party (Main Street)

September 2, 2016  6-10pm

Main Street goes car-free and becomes a destination for evening fun, with free entertainment, live music, great food, children's activities, contests, games, and more.

​Gloucester Schooner Festival

September 2-4, 2016

Gloucester Schooner Festival - Gloucester MA - Fall Breaks

This is THE event of the season in Gloucester! This 3-day festival over Labor Day Weekend is a major maritime and sailing event. Organized by the Gloucester Schooner Festival Committee and Maritime Gloucester, the schedule includes the Maritime Gloucester Gala, a Lobster Bake, free exhibits at Maritime Gloucester, boat parades, fireworks and of course, the Mayor's Race off Eastern Point for the Esperanto Cup, Ned Cameron Trophy and Betty Ramsey Trophy.

Newburyport's Riverfront Music Festival

September 3, 2016,  Noon to Dusk

15th Annual Riverfront Festival in Conjunction with WXRV - 92.5 The River and the Greater Newburyport Chamber of Commerce & Industry. Spend the day on the waterfront in Newburyport and enjoy great food & shopping in addition to the concert.

Newburyport Lantern Festival - Fall BreaksNewburyport Lantern Festival
September 4, 2016, 6:00 - 8:00 PM

​The Newburyport Lantern Festival, sponsored by Greater Newburyport Ovarian Cancer Awareness, will be held at Bartlet Mall, Frog Pond, Newburyport. Inspired by Asian traditions, families and friends will be remembered and wishes made for the future as lanterns are dedicated and then lit and floated on the pond at dusk. 


Trails & Sails: Two Weekends of Walks and Water

September 16-18 & 23-25, 2016

A series of FREE events located within the 34 cities and towns of Essex County including the communities of Salem, Essex, Gloucester, Newburyport, and Rockport. For full calendar of events, go to:

Beverly Block Party, Cabot Street

September 17th  5:30-9:30pm 

Beverly’s downtown street party will take place on Cabot Street from Pond Street to Federal Street where guests can walk around, meet up with friends, listen to live music and enjoy street food. 

Gloucester Harvest Music Festival - Fall Breaks​Gloucester Harvest Music Festival

September 17th, 11am – 9pm

The Gloucester Harvest Music Festival blends art and music in one of the country’s most unique and rich artist communities. You’re invited to experience Gloucester via this day-long festival showcasing music, arts and culture while supporting our local community hospital (Addison Gilbert Citizens Fund) and community based outreach programs.


October Events on Cape Ann / North Shore

Cape Ann Plein Air 1st Annual Painting Competition And Festival

October 10th-16th, 2016

Cape Ann Plein Air Festival - Fall BreaksFor nearly two centuries, Cape Ann has been a destination for some of the finest painters who paint out-of-doors, or "en plein air." Cape Ann Plein Air will host a week long plein-air painting celebration in October when the famous Cape Ann light shines at its very best. Organized by the Cape Ann Chamber of Commerce, seARTS, and Cape Ann’s leading arts and culture organizations, the communities will see up to 40 of the finest artists in the nation compete for $16,000 in prizes and awards. The work produced will be sold at the Grand Awards Gala on Saturday, October 15 at the Rockport Art Association & Museum.


Gran Prix of Gloucester
October 15-16, 2016

Cyclocross is a type of bike race that involves a challenging grass, dirt and asphalt racecourse with obstacles. The Gran Prix of Gloucester bring competitors from all over the US, Canada & Europe to race at Gloucester’s own Stage Fort Park.

Rockport HarvestFest

October 15, 2016, 10am -6pm

The annual Rockport HarvestFest is a family-focused event featuring live music, kids' art activities, a showcase for non-profits and community organizations, the annual Scarecrow Stroll and the centerpiece of the festival: the Local Fare Fair, which highlights our amazing Cape Ann and New England food producers. Don’t miss the Seafood Throwdown, a competition-style showcase between two chefs, demonstrating the versatility of fish, coastal New England’s most significant harvest.  

Essex Clamfest - Essex MA - Fall BreaksEssex Clamfest & Clam Chowder Competition

October 22, 2016 11am-4pm

In addition to the Chowder competition, activities include an arts and crafts area and vendors providing food and fun. Entertainment available throughout the afternoon, including rides and games for children and a health and wellness fair. 


Fall vacation rental rates start going down in September, so book your stay today!


Call our Guest Experience Specialists toll-free at (888) 973-3864 or book online.


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Atlantic Vacation Homes (AVH) is the premier vacation rental & real estate company on Boston's North Shore, with over 30 years of creating dream vacations for our guests. Situated a little more than a half-hour’s drive from downtown Boston, the North Shore is the ideal spot for an east coast beach vacation. We specialize in vacation rental homes for families & large groups as well as anyone else who wants to vacation near the shore.