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Head of the Charles Regatta
Oct 20th, 2018 to Oct 21st, 2018
Boston / Cambridge, MA

Head Of The Charles Regatta®, the world’s largest two-day rowing event, was first held on October 16, 1965. The race was established by the Cambridge Boat Club members with the advice of Harvard University sculling instructor Ernest Arlett. Arlett proposed that a “head of the river” race, similar in tradition to races held in his native England, be held on the Charles River. “Head” races, a class of regattas, are generally three miles long – boats race against each other and the clock, starting sequentially approximately fifteen seconds apart. Winners of each race receive the honorary title of “Head of the River” or, in this case, “Head Of The Charles.” Today, more than 7,500 athletes from around the world compete in 55 different race events. The Regatta grew to a two-day event in 1997 and now attracts up to 300,000 spectators during the October weekend. 

Boston Christmas Festival and Gingerbread House Competition
Nov 02nd, 2018 to Nov 04th, 2018
Boston, MA

This annual Christmas festival features the distinctive work of more than 300 master American craftsmen. Bargain hunters, as well as those with extravagant tastes, will find an endless array of gorgeous home accessories, designer fashions, artisan jewelry, handcrafted holiday décor, gourmet specialty foods and one-of-a-kind handcrafted gifts unavailable elsewhere. Don’t miss the popular Gingerbread House Competition, a crowd favorite showcasing the amazing talent of Boston’s top chefs. Go online for a discount coupon.

The Great Mac and Chili Challenge
Nov 04th, 2018
Sherwood Island State Park
Westport, CT

Those who attend, get to judge who has the best classic and creative chili along with classic and creative mac & cheese. Everyone gets a spoon, pencil and a ballot when they check in. Then enjoy unlimited sampling of 20 different chili and mac & cheese entries. Admission is just $15 for adults and $5 for kids (6-12), parking is FREE and the event is rain or shine. Tickets are available at the door or online at

Equine Affaire
Nov 08th, 2018 to Nov 11th, 2018
Springfield, MA

Experience the nation's premiere equine exposition, featuring more than 230 unique clinics, seminars, and demonstrations by top professionals in the horse industry. Equine Affaire also hosts the largest trade show in the East, showcasing hundreds of commercial exhibits, an extensive Breed Pavilion, a fun-filled Youth Pavilion, the Versatile Horse & Rider Competition, and a special evening show - the Fantasia, a musical celebration of the horse. 

Christmas Festival of Lights at Edaville USA
Nov 15th, 2018 to Dec 29th, 2018
Edaville USA Theme Park
South Carver, MA

Edaville USA’s most memorable New England Tradition is back this year with over 17 million lights illuminating the park! Admission includes Edaville USA’s 3 Adventures in 1; Edaville Proper, Thomas Land & Christmas Festival of Lights, featuring 90+ rides & attractions! Yes, the rides are open! See the website for exact dates.

Blackstone Valley Polar Express
Nov 16th, 2018 to Dec 23rd, 2018
Woonsocket, RI

A 90-minute train ride on the Providence & Worcester Railroad. Enjoy story reading of the Polar Express; hot chocolate and cookies, special Christmas gift; coloring books and crayons, and a holiday sing-a-long. Visit the holiday shop under the tent! Be sure to bring a camera for photos with Santa! Event happens on Friday, Saturday, and Sunday only.