Festive Fall Outings In and Around Boston
Some of us here in Boston may not be ready for the changing weather, but the changing leaves have started to tell us that summer is definitely over. Once we get over the initial cold mornings, I think every Bostonian has a deep appreciation for the beautiful fall atmosphere in New England. So grab a sweater and join us for some of our favorite regional fall festivities!
September:
ArtWeek Boston:
This new Boston venture kicks off on September 27th and runs the full week. Attendees can experience art and entertainment from every end of the definition all across Boston’s neighborhoods. Set up like a quasi-Restaurant Week, experiences are priced prix-fixe with prices starting at FREE!
Beantown Jazz Fest:
An annual event hosted by Berklee College of Music, is Boston’s biggest block party! A completely free, completely outdoor festival – Bostonians and visitors alike, look forward to this musical event. This year’s festival is on Saturday 9/28 and the theme is : ‘Jazz: The Next Generation’, featuring some acclaimed, up and coming artists!
October:
Food Truck Festival:
Boston has come to love our Food Trucks, and Food Trucks love Boston! Come celebrate the fabulousness of gourmet food from a truck! Remaining dates are Saturdays 9/21, 10/5, and 10/26 in Brighton, Barnstable, and Providence, RI.
Apple Days:
The Boston area is bursting with Apple Orchards and ‘U-Pick’ opportunities, but on the weekend of 10/5 and 10/6, head out west (Western Massachusetts that is) to Old Sturbridge Village where you can take in the sites of this classic, small New England town, and take part in Apple Days! A weekend of everything apple; from apple cider, to apple picking, to apple pressing, and even a beehive exhibit. There is no better way to welcome Fall!
Haunted Happenings:
October means a month of festivities for our history-packed Salem Massachusetts. Not far out of Boston, this little town was the site of the Salem Witch trials in 1692 and the location of Arthur Miller’s The Crucible. So dawn a costume (or not) and take the short ride out to Salem to check out their witch museums, new-age Wiccan shops, and all sorts of scary fun! Something new every weekend in October
Oktoberfest in Harvard Square:
Cambridge is our sister-city of eclectic restaurants, residents, and a few renowned universities (you may have heard of Harvard?). Every year, Harvard Square, one of the most entertaining sections of Cambridge, puts on an Oktoberfest Celebration like only Harvard Square can do! So on October 12th, Grab your lederhosen and head over for the parade, some vintage shopping, bratwurst, and brews!
Opening our Doors, Fenway Culture District:
The Red Sox have made Fenway a famous name to many, but the area of Fenway has many other things to offer as well! On Monday the 14th you can witness first-hand what those things are as 22 institutions of rhe Fenway Alliance work to put on the largest single day of FREE cultural experiences in Greater Boston! Over 60 activities across 17 indoor and outdoor venues, you won’t be bored, or sorry you came! The day begins at 10am on the Mass Ave side of the Christian Science Plaza.
Head of the Charles Regatta:
Image from Boston Magazine
A very famous annual Boston event, come join the masses on the 19th and 20th to view the 49th race of the world’s best Crew Teams as they power themselves along the Charles River. The event attracts over 9,000 athletes each year, and there, is much in addition to the competition, to keep the 300,000 spectators entertained. Check out Reunion Village at the center of the course to grab some eats and refreshments, or the Rowing and Fitness Expo at the finish line. There is also the Weld Exhibition all along the banks with official vendors with everything from merchandise to food.








