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Boston's Best Fall Festivals

Simply because the summer is over, doesn't mean the outdoor fun has to end. Boston's fall festivals were designed to keep the party going long after school kicks back up. Many of these events take place right in the heart of the city, offering a wonderful way to enjoy a mix of family fun and enjoyment well into the autumn months.
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8th Annual Hub On Wheels Bicycle Festival
City Hall Plaza
Downtown Boston, MA
(617) 918-4456

Sunday, Sept. 23 – 6:30 a.m. to 7:45 a.m. registration and packet pickup; 7:45 a.m. opening ceremony; 8 a.m. start
Price: $45 registration fee on site day of event or online

There's no more memorable way to experience Boston than by participating in the city's annual Hub On Wheels Festival. This one-day event offers cyclists a unique chance to see the city in ways they might never otherwise explore. This city-wide experience allows cyclists to explore historic neighborhoods, ride along a car-free Storrow Drive and enjoy unmatched views of the Boston Harbor. The ride starts and finishes at City Hall Plaza, utilizing three scenic routes that are 10, 30 and 50 miles in length. Rent a cycle if you don't have your own for a truly exciting way to explore this city.

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Asian Music and Culture Festival
Berklee Performance Center
136 Massachusetts Ave.
Boston, MA 02115
(617) 747-2261

Wednesday, Sept. 26 – 8:15 p.m.
Price: $8 in advance/$12 day of show

This exquisite event hosted by the Berklee Performance Center highlights the uniquely beautiful music and culture of Asia's many regions. This always-popular festival brings together some of the best of Asian music and culture in one location for one truly fascinating and entertaining evening that's certain to be a memorable one. Last fall, attendees to this great event enjoyed both traditional and contemporary selections from diverse locations including Thailand, India, Pakistan, Bangladesh, Korea, Japan, China, Mongolia, Indonesia and Vietnam. This year's presentation promises to be equally as entertaining, featuring a mix of diverse music honoring the old traditions while embracing newer styles.

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Boston Local Food Festival
The Rose Kennedy Greenway near The Wharf District and American Heritage Parks
Boston, MA
(617) 575-9165

Sunday, Oct. 7 – 11 a.m. to 5 p.m.
Price: free

If you love tasty food and fun with a home-grown flavor, you won't find a better combination of the two than at the Boston Local Food Festival. This unique festival brings local farmers, food businesses and specialty producers together with everyday folks for a great time. It provides an opportunity to sample, savor and learn about the benefits of locally produced, healthy food. This festival provides a diverse menu of festivities, exhibitions, music, and arts and crafts for both young and old.

Related: Boston's Best Historical Sites

photo credit: head of charles regatta

48th Head Of The Charles Regatta
Banks of the Charles River
Boston, MA
(617) 868-6200

Saturday, Oct 20 to Sunday, Oct. 21
Price: free

One of Boston's signature fall events is about to celebrate its 48th year of bringing rowers and spectators from around the globe to the banks of the city's beautiful Charles River. Thousands are expected to attend and participate in this uniquely Boston event that combines athleticism, fun and excitement as spectators watch rowers race along the waters of the Charles. Events, expos, exhibits and presentations galore line the Charles during this exciting two-day party. Whether you are the member of a rowing crew team or simply a casual spectator, The Head Of The Charles Regatta is a Boston tradition that must be experienced again and again.

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Fall Wine Festival
Cyclorama at the Boston Center for the Arts
539 Tremont St.
Boston, MA 02116
(781) 444-7771

Saturday, Nov. 3 – noon to 2:30 p.m.; 3 p.m. to 6 p.m.; and 7 p.m. to 10 p.m.
Price: $59

Whether you're a wine connoisseur or simply a casual taster of the fruit of the vine, the Fall Wine Festival always brings flavors that tease, tempt and appeal to every palate. Guests visiting this popular event will be given a passport to visit areas representing regions from around the world, where they can sample each area's native wines. This is a wonderfully social, interactive event geared toward young professionals seeking to mix, mingle and savor fine wine while making new friends. Membership to the event is required, but is free of charge and easily available at the event website.

Related: A Great Year for Travel in Boston

Tim Estiloz is an experienced, two-time Emmy-winning TV journalist / performer with over a decade of covering entertainment news and features. Based in Boston, Tim is also a voting member of the prestigious Broadcast Film Critics Association which awards the annual Critics' Choice Awards in Hollywood. Tim has interviewed and profiled dozens of Hollywood's top Oscar-winning film and television actors, including Meryl Streep, Will Smith, Kate Winslet, Brad Pitt and more. Actor/director Ben Affleck also cast him for a speaking role as a TV reporter in his critically acclaimed film "Gone Baby Gone." Find his work on Contact him direct at or follow him on Twitter @TimEstiloz

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