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The Topsfield Fair
Sep 28th, 2018 to Oct 08th, 2018
Topsfield, MA

This event is the quintessential country fair — traditional agriculture, big entertainment, rides, games, shopping, and great food … something for everyone! Established in 1818, America’s oldest continuously running agricultural fair opens with the famed New England giant pumpkin weigh-off (in 2012, the 2,009-pound heavyweight champion became the world’s first 1-ton pumpkin). Come see horse and dog shows, a circus, crafts and farm animals of all kinds.

Octoberfest at Harpoon Brewery
Sep 28th, 2018 to Sep 29th, 2018
Harpoon Brewery, MA

Harpoon Brewery’s annual German-style OctoberFest boasts three stages with live music, a big selection of Harpoon beers and ales, and lots of German food sold by a local restaurant. Come do some chicken dancing and keg bowling and enjoy the German Oompah bands at one of New England’s largest OctoberFests.

Berklee Beantown Jazz Festival
Sep 29th, 2018
Boston, MA

The Berklee BeanTown Jazz Festival delights tens of thousands with a host of jazz, Latin, blues, and groove acts. The city comes out in force to enjoy world-class jazz on three stages, great eats, and good times stretching six blocks in Boston’s historic South End.

Annual Burke Fall Foliage Festival
Sep 29th, 2018
East Burke Village, VT

Head to northern Vermont for brilliant autumn colors and the Northeast Kingdom’s biggest event: the annual Burke Fall Foliage Festival. Shop for local crafts from more than 60 vendors, see the parade at 10 a.m, plus a rubber ducky race, live music, horse-drawn wagon rides, a farm animal petting zoo, Cow Plop Bingo, a beer & wine tent, live musical entertainment and more! Read more about the event here.

Sep 30th, 2018
Sherwood Island State Park
Westport, CT

Discernible foodies travel far and wide to attend this annual event that determines the best chowder, soup and bisque in New England and take advantage of the “Stay and Slurp” hotel and ticket package. 40 award winning restaurants with every New England state represented! You're the judge in this unique "fun"raiser in the ongoing fight against hunger! You'll get a spoon, ballot & pencil – enjoy unlimited sampling and then rate your favorites! Four categories to judge: New England Clam, Manhattan/Rhode Island Clam, Creative Chowder and Soup/Bisque.

The Fryeburg Fair - Maine's Blue Ribbon Classic!
Sep 30th, 2018 to Oct 07th, 2018
Fryeburg, ME

Come to the largest agriculture fair in Maine – eight days of entertainment and education for the whole family. See a variety of livestock, draft show horses and ponies, pulling horses and oxen, sheep dog trials and a huge parade on Saturday. There’s a thrilling midway with amusement rides and delicious food, live music all day and nightly entertainment. The Fair attracts upwards of 300,000 visitors each year. There are 3,000 campsites onsite.