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Top Events to Enjoy in Boston and Greater Boston This October

October in Boston is a magical time, with fall foliage painting the city in vibrant colors and the crisp air signaling the arrival of sweater weather. From festive fall activities to cultural events and Halloween fun, there’s no shortage of things to do in Boston and Greater Boston this October. Whether you’re a local or visiting the city, here are some must-attend events to mark on your calendar.

1. Head of the Charles Regatta (October 19-20, 2024)

One of the most iconic events in Boston, the Head of the Charles Regatta draws thousands of athletes and spectators to the Charles River for this two-day rowing competition. The event features more than 11,000 athletes from around the world racing along a scenic 3-mile course. Whether you’re a rowing enthusiast or just love a festive outdoor atmosphere, the Head of the Charles is a quintessential fall event in Boston. Don’t miss the vibrant displays of fall foliage along the riverbank!

2. Salem Haunted Happenings (All October)

Just a short trip from Boston, the historic town of Salem is the ultimate Halloween destination. Salem Haunted Happenings runs throughout October and features a month-long celebration of all things spooky. From haunted house tours to witchcraft history, costume parades, and psychic readings, Salem transforms into a Halloween wonderland. Don’t miss the Salem Witch Museum and the city’s lively Halloween Night Festival on October 31st, where the streets are filled with revelers in elaborate costumes.

3. Boston Food Truck Festival (October 26, 2024)

If you’re a foodie, the Boston Food Truck Festival at the Boston Seaport is a must. Dozens of Boston’s top food trucks will be serving up a variety of dishes, from gourmet burgers to tacos, lobster rolls, and ethnic cuisine. Enjoy live music, entertainment, and local craft beer as you sample the best mobile eats the city has to offer. This family-friendly event is a great way to enjoy delicious food while taking in the beautiful Seaport waterfront views.

4. Fall Foliage Walks and Hikes

October is the perfect time to take in New England’s famous fall foliage. Boston and Greater Boston offer plenty of scenic spots for a fall hike or leisurely walk. Arnold Arboretum, located in Jamaica Plain, offers stunning views of changing leaves across its 281 acres. For those looking for a more adventurous hike, head to Blue Hills Reservation in Milton, where you can enjoy panoramic views of the Boston skyline amidst a backdrop of fiery red and orange trees.

5. Boston Fall Pumpkin Float (October 20, 2024)

For a family-friendly, whimsical event, check out the Boston Fall Pumpkin Float at the Boston Common Frog Pond. Bring a carved pumpkin to float on the pond and watch as hundreds of glowing jack-o’-lanterns drift across the water. This free event also features spooky music, crafts, games, and plenty of photo opportunities. It’s a fantastic way to celebrate Halloween with kids.

6. Beacon Hill Halloween Stroll (October 31, 2024)

Experience Halloween in one of Boston’s most historic neighborhoods during the Beacon Hill Halloween Stroll. With its cobblestone streets and gaslit lanterns, Beacon Hill transforms into a Halloween haven. Families from all over the city gather to trick-or-treat in the beautifully decorated homes, while neighbors go all out with elaborate haunted displays. It’s a picturesque and spooky Halloween tradition you won’t want to miss!

7. Apple Picking at Honey Pot Hill Orchards (All October)

Fall in New England isn’t complete without a classic apple-picking adventure. Just a short drive from Boston, Honey Pot Hill Orchards in Stow offers apple picking throughout October, along with hayrides, corn mazes, and cider donuts. It’s a fun-filled day for families, couples, and anyone looking to embrace the fall season. Be sure to try their famous caramel apples and homemade apple pies!

8. The Boston Halloween 5K (October 27, 2024)

For those who enjoy staying active, the Boston Halloween 5K is a fun way to get in the Halloween spirit. Runners dress in costumes and take on a 5K course through Boston’s streets. It’s a lively race, with plenty of spectators cheering runners on, and prizes for the best costumes. Whether you're a seasoned runner or just in it for the fun, this race is a unique and festive way to celebrate Halloween.

October is a fantastic month to explore all that Boston and Greater Boston have to offer, with events ranging from cultural festivals to spooky Halloween celebrations. Whether you’re taking in the fall foliage, attending a festive event, or exploring the rich history of the area, there’s something for everyone to enjoy this autumn.

Looking for your next home in Boston? Contact us today to find your perfect place to enjoy all that Boston has to offer in the fall and beyond.

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