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October Events in Boston

What to do in Boston in OctoberBoston October Events 2019

Things to Do in Boston in October 2019

Soak in the beautiful weather beneath the October skies of Boston. October means Halloween and with its many historic graveyards, ghost stories, not to mention of pumpkins from the surrounding New England farms & orchards, Boston is a great place for  Halloween, with celebrations and special events going on all month. 

Head of the Charles Regatta

Enjoy the day at the Head of the Charles Regatta  and experience one of the world's largest rowing events.  Watch rowing teams compete from all over the country and take in the  breathtaking sights of autumn along the banks of the Charles River in Cambridge.  You'll find the best viewing areas for the event on Memorial Drive between JFK Street and BU Boathouse.

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Enjoy the festivities at Illuminus, the free nighttime festival where Boston's performers, artists and designers come together to show off their brilliant works.

Fall Pumpkin Float Festival at Frog Pond

Boston's annual Fall Pumpkin Float is held at the Boston Common Frog Pond.  Hundreds of illuminated jack-o’-lanterns are floated on the water accompanied by spooky family activities. 

Photo credit:  Boston Frog Pond

Attendees are asked to bring 8-inch or smaller carved pumpkin that will be lit and then floated on the Frog Pond for a dramatic early evening display.  Adults and children are encouraged to wear Halloween costumes and participate in a wide range of fun activities.

Annual DCR Neponset Pumpkin Float

Bring a pumpkin to ⁦‪Pope John Paul II Park and enjoy an evening of family-friendly fun at the annual Neponset Pumpkin Float!  This fun Dorchester tradition includeds hundreds of costumed children and their families, as well as enthusiastic individuals will participate in the floating parade of illuminated jack-o-lanterns down Davenport Creek to the Neponset River.

Participants can bring a 6 – 8 inch hollow pumpkin that has been carved at home to the Hallet Street entrance to the park to be mounted on a special individual float.  Each jack-o-lantern will have a candle inserted and lit before being launched en mass in the water at 6:00 pm.  Floats and candles are provided, resulting in a beautiful water parade of spooky pumpkins.
 

Boston Columbus Day Parade

March on over to Boston's spectacular Boston Columbus Day Parade! The iconic parade features an eclectic mix of marching brass bands, military units and Colonial militias, Italian-Boston organizations, Duck Boat floats, politicians, other entertainers, and even vintage cars!

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October in Boston often means overlapping sports seasons.   So if baseball isn't your things, grab a foam finger and cheer on the New England Patriots at Gillette Stadium!  

Take a Spooky Tour

Get your spooky on with the Ghosts & Gravestones Tour.  You'll be guided by a ghoulish band of the undead and a roguish gravedigger as you ride  the Trolley of Terror that travels back in time as you relive grisly murders, heinous torcherings and cold-blooded executions like the ones that took place on the Boston Common.

HONK! Festival 

HONK! Fest is a rousing socio-political music spectacle which features social activist street bands from all over the world, who come together to share their different approaches in merrily instigating positive changes in their communities.

Jack 'o Lantern Displays & Festivals

Don't miss the Jack o' Lantern Spectacular at Roger Williams Zoo this October!  Filled with “gourdly” grandeur the zoo is illuminated with thousands of festive pumpkins that are carved with impressive artistry and creativity for viewers to marvel at.

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Photo courtesy of Providence Warwick Convention & Visitors Bureau

Come see thousands of Jack-O-Lanterns at the annual Camp Sunshine Pumpkin Festival in Weston.  Enjoy a movie Friday night, and on Saturday have a day filled with family fun, kids games, pumpkin carving, great tunes, face painting, a costume parade and much more!  The family friendly event features live pumpkin carving demonstrations, a pumpkin patch, fall food and beverages, and other fun interactive experiences for the whole family.

Celebrate Halloween at Science Tricks and Animal Treats at the Ecotarium! Join our educators for sneaky science programs about animal camouflage, invisible forces, and secret powers, then join our wildlife keepers to learn about the treats and training that enrich our resident animals lives. 

Pru Boo!

Trick-or-Treat for Charity at Prudential Center's annual Pru Boo!  Calling all ghosts and goblins to join the fun at this spooktacular family-friendly Halloween event, held the Sunday before Halloween.  Each year, parents are invited bring children to trick-or-treat at over 50 participating stores and restaurants. Other activities include face painting, magic shows, and activities by local Boston attractions.

Boo at the Stone Zoo!

Children throughout New England are invited to trick-or-treat among the animals at Stone Zoo's Annual Boo at the Zoo event. This fun filled event will feature Halloween themed crafts and games, along with a haunted maze.  Throughout the day, guests can learn about the importance of enrichment as they watch many of the animals receive pumpkins.

Zoo Howl at Franklin Park Zoo

During this popular Halloween event, children throughout New England are invited to trick-or-treat among the animals at the Franklin Park Zoo.  Other haunted happenings at Zoo Howl include creepy crafts, ghoulish games, costume contests, storytimes, puppet shows, and a haunted maze!  

Salem Haunted Happenings

Head to the bewitching seaport of Salem, Massachusetts and get your spirits humming at Haunted Happenings, America's Halloween Festival. Nobody celebrates Halloween quite like Salem in the month of October.  It's a fantastic place to see some amazing costumes, parades, and enjoy special events. 

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Topsfield Fair

Enjoy The Topsfield Fair, America's oldest and finest agricultural fair w/ New England‘s largest carnival midway, cool demos, (ranging from beekeeping to miniature trains), a Grange Museum, pumpkin weigh-offs, live entertainment and the 4-H Agricultural/Arts and crafts exhibits.  About an hour north of Boston, this is a fun fall tradition that is terrific for all ages.  

Davis Mega Farm Festival & Corn Maze

Fall in New England means corn mazes and hayrides and outdoor fun.  Flaunt your navigation skills as you maneuver your way through an intricate corn maze.  Other activities include knocker soccer and quad carts to corn cannons and archery tag; OR you can simply sit back, relax and listen to some live music, Davis Mega Farm Festival is a fun, seasonal outing for the entire family!

Photo courtesy of Davis Farmland Mega Maze

Fall Foliage

As the leaves start to transform into the picturesque hues of gold and crimson, New England truly puts its best foot forward.   Check out some of our favorite Great Spots to View Fall Foliage and discover the splendor of the trees.  Be sure to bring your camera along, as the breathtaking Fall foliage provides an unmatched backdrop for photographs.

fall-foliage-near-boston-october

Apple Picking, Hay Rides and Pick Your Own Farms

Head to local farm for pick-your-own variety of fun and deliciousness.  Apples raspberries, peaches, pears and more, whatever happens to be in season.  Visit their on site farm markets for specialty items and baked goods to satisfy your farm fresh cravings.  

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Introducing your family to gardening through pick-you-own farm locations is a great way to get everyone in touch with nature and to value our locally grown foods. Check out some of these great local farms  which also feature playgrounds and this list of must-visit corn mazes for continued family fun.

Nothing says Fall like pumpkin picking with the family! Whether you want to carve, paint, display or even eat pumpkins this Fall,  there is no shortage of patches to pick from and more picturesque New England landscapes than in the Boston area.

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Take a Guided Tour

With the crisp and clear days of October ahead of you, it's the perfect time to take full advantage of the outdoors and historic Boston with a guided tour.  The tours on our list are sure to please your senses, gain some knowledge and in some cases even tantalize your tastebuds!

You won't find a sweeter way to spend the day in Boston than on a Boston Chocolate Tour.  A chocolate tour means exactly that with the addition sweet treat of chocolate samples along the way! The only thing that sweetens the deal even more is that there are several tours to choose from in a variety of neighborhoods!

boston-chocolate-tour

Join in on a Boston Segway Tour,  Boston's most sought-out attractions in touring the city, leading the way with a premier service that shows guests the city of Boston in a way like never before. See the city in a short amount of time - while learning Boston's history, creating fun memories, and best of all... while riding your own personal Segway PT!

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Photo courtesy of Boston Segway Tours

Step right up onto the field and explore behind the scenes on a Fenway Park Tour! Learn lots of fascinating facts about the Red Sox and their history and the stories from years past.  Experience everything Red Sox on this very popular Boston Tour.

Take an unforgettable 90 minute walk through history as you follow the 2.5 miles of Boston's Freedom Trail via a walking tour.  Follow the famous red brick path to 16 historic sites through Boston's most historically well known neighborhoods and dive into Boston's rich history and America's path toward liberty.

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Finally, you should explore the North End, Boston's oldest neighborhood settled in 1630 on the  Boston Pizza Tour.   Italian is still spoken in the quaint, cobblestone streets of this historic area.  Enjoy three amazing slices of Boston's best pizza, and view five historical sites along Boston's Freedom Trail.    

Find more things to do next month in our November events in Boston guide.   And for a daily view of what's going on in Boston - visit our Boston Events Calendar any time of the year.