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10 Things To Do Around Boston For Fall

Looking for some fun and spooky ways to spend your October in Boston? East Coast Realty has pulled together our top ten fall activities around the city happening this month. Whether you're a Boston local or are in town searching for a new apartment, check out one or all of these events!

View from above at an Oktoberfest Beer hall full of people

Oktoberfest Celebrations

Throughout Boston + Cambridge | First and Second Weekend of Oct.

Looking for a way to celebrate Oktoberfest? Boston has a number of celebrations going on throughout the month of October. Be sure to check out Harvard Square, Harpoon Brewery, the Samuel Adams Taproom, Time Out Market or Trillium Brewery at any location! You can find delicious food, great Oktoberfest beer, arts and crafts vendors, family friendly activities, and music.

Doggone Halloween Parade

Downtown Crossing | Saturday Oct. 29th @ 12pm

Goldendoodle puppy dressed as a ghost posing with three pumpkins

Enjoy one of the cutest events Boston has to offer in Autumn: the Halloween Dog Parade. Located in Downtown Crossing, dogs are dressed up in Halloween costumes and are paraded around for everyone to see. Some of the awards given out are: Best Costume, Cutest Costume, Scariest Costume, or Best Dog & Human Duo. Grand prize winners are selected by celebrity judges.

This is definitely a can't miss event in Boston, especially since it's free!

Pumpkin Picking at Allandale Farm

259 Allandale Road Brookline, MA 02467 | Open Tues - Sat: 9am-6pm, Sun: 10am-5pm

A pile of orange pumpkins on a hay bail

Did you know there’s a pumpkin patch right here in Boston? Allandale Farm is located in Brookline, and offers some of the best pumpkins in the city, as well as tons of other produce and a lush garden center. They offer events throughout the year, including Story Time on the Hill Every Wednesday at 11am, July through October. Follow Allandale Farm on Instagram to keep up with their seasonal events and fresh goods! @allandalefarm

Trip to Salem, MA

Events and Tours All Season Long

Salem, Massachusetts is a very popular attraction as it is where the Salem Witch Trials took place. This is one of the spookiest towns in the country because of its history. You can find an array of restaurants, cute shops, tours, and activities. Salem is located approximately 45 minutes outside of Boston. This is the perfect place to get you in the Halloween/Fall spirit!

The “Witch House” located in Salem Massachusetts decorated for Autumn

Head of the Charles Regatta

On the Charles River between Cambridge and Boston | Oct. 21-23 | Best Place to Watch

Rowers competing in the “Head of the Charles” regatta in Boston

The Head of the Charles Regatta is one of the world's largest rowing events. Here, you can see people from all over the country compete along the banks of the Charles River in Cambridge. Winners of each race receive the honorary title of 'Head of the River' or, in this case, 'Head Of The Charles.' Each year, this event attracts over 300,000 spectators.

Check the link above to find the best viewing spots along the Charles River!

Apple Picking at Shelburne Farm

106 Acton Road Stowe, MA 01775 | 9am-5pm Weekdays, open til 6pm on Weekends

Two people carrying a barrel of freshly picked apples

Having a hard time finding a place to go apple picking? Shelburne Farms is located in Stow, which is an hour outside of Boston. This farm has apples and pumpkins that you can pick yourself, along with food trucks on certain days, hay rides, farm animals, cider making, and children’s play areas. This is the perfect spot to enjoy the Fall season!

Columbus Park Fall Festival

Columbus Park in the North End | Sat. Oct. 15 12pm-3pm

Dress up in your best Halloween costume or fall attire and come out to see live music and entertainment in Columbus Park! Play lawn games, pick pumpkins, and participate in many more fall activities, including a children’s parade! “Fall” in love with the North End while you’re there? Check out available apartments in the area on RentWise Boston.

Barrett's Haunted Mansion

1235 Bedford St., Abington, MA 02351 | All October Long

Old red antique lamp with spider webs

Located off of the Kingston Commuter Line in Abington, MA is Barrett's Haunted Mansion. Celebrating 31 years of frights and fun, Barrett's offers events almost every night of this month, including 18+ Devil's Night, and open air attraction and behind the scenes tours! Stop in at The Abington Ale House next store for dinner and drinks before you head into Barrett's Mansion.

Fall-0-ween Children's Festival

38 Beacon St. Boston, MA 02108 October 21, 5 - 8 p.m.| More information here!

Gather up the little ones and pay a visit to Boston Common's Frog Pond Friday October 21st to celebrate the season at the Fall-o-ween Children's Festival! Put on by Boston's Parks and Recreation department, this fest is full of free family friendly activities to participate in all night long. There will be spooky games, refreshments and don't forget to wear your costumes- you too parents!

Fenway Halloween Bar Crawls

Landsdowne Street, Fenway Area | Multiple throughout the weekend of the Fri. 28- Mon. 31

Looking for a fun 21+ activity in the Fenway area for Halloween weekend? Checkout the bar crawls going on the weekend of October 28th-31st. Some of the bars participating in this event are Cheeky Monkey Brewing, Lucky Strike, and a couple others on Lansdowne Street. There will be Halloween themed drinks, live music, food, an after party, and some of the best costumes in Boston. You can even participate in the social media contest where the winner will be chosen for having taken the best photos and videos of the event. You can win cash and prizes!

Looking for A New Home?

Check out our platform RentWise Boston, where you can find real-time listings that are checked twice to ensure an accurate representation of the Boston Market!

Need help with buying or selling a home? Contact one of your agents today.

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