Boston in October: 25 Best Things to Do, Weather, Cost and Tips for Boston in October

Boston is one of the oldest cities in America and the largest city in Massachusetts. The rich history, sports enthusiasm, and commendable education make Boston a worthy city for a cool weekend visit. Boston is famous for strolls and bike rides, and the popular baked beans dish- naming the city ‘Beantown’ for the same. Beantown in October is even better for experiencing all the fun activities and places of the city. 

Weather in Boston in October

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The weather of Boston in October is mid-fall, where summers have started to descend, and winters are just on the threshold. The average high temperature ranges from 67℉ to 57℉ (19℃ to 13℃). The average low temperature ranges from 53℉ to 43℉ (12℃ to 6℃). October brings in the season of fall- it’s warm and pleasant in the day and cool in the night. It’s a lovely sight to behold.  October is the perfect time to visit Boston. There are several events and games to attend, and there is no problem with the weather. Along with experiencing Halloween, tourists witness Boston at its finest during this month. There are sidewalk cafes, basketball games, and outdoor concerts that will make your stay worthwhile. 

Cost

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Since Boston invites a horde of tourists to the city, the hotels and arenas make money. It is slightly more expensive to visit Boston during this time since it’s the peak season, but the fun and cruise of the city will make the expenses worthwhile. You can save money by walking and cycling around the city, and booking hostels. Stick around for more tips about Boston in October at the end of this article!

October invites a plethora of events in the city. Ranging from playoff season to Oktoberfest, you won’t get enough of this city. The New England location of Boston gives it a very orange-aesthetic vibe all over. Check out the top things to do in the following list!

Things To Do in Boston in October

Boston in October has a lot of fun events to attend and places to go to. The entire city is basking under the fall leaves, walking to art exhibitions, and enjoying the game spirit. The city itself offers several events and fests to look out for, check them out!

Best Events and Games to Attend in Boston in October

1. Oktoberfest

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Oktoberfest is celebrated at various locations in Boston. Majorly expanded over the first couple of weeks, various locations have various activities in place, with music, food, dance, and of course- beer. Two of the most popular locations for Oktoberfest in the city: 
A. Harvard Square
Harvard Square’s Oktoberfest includes food, arts and crafts, vintage goods from all over the world, five beer gardens, sidewalk sales, live music, and their HONK! parade on four different stages.
Location: Brattle St, Cambridge, MA 02138
B. Harpoon
Harpoon Brewery’s Oktoberfest includes varieties of beer, oompah music by new bands, and of course a lot of dancing. It is a premium festival to visit if you love beer.
Location: 306 Northern Ave, Boston, MA 02210

2. Columbus Day Parade

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Columbus Day Parade is one of the biggest celebrations in Boston. It celebrates Boston’s Italian history, the adventures of Christopher Columbus to America, and the commitment of Massachusetts military units to American freedom. The parade occurs on the Sunday before Columbus Day, in North Boston in odd-numbered years (2021, 2023, 2025), and in East Boston in even-numbered years (2022, 2024, 2026). 

This event is completely free and is met by a swarm of marchers, brass bands, military units, Duck Boat floats, organizations and societies, politicians, vintage autos, drums, bagpipes, and more. There are various sales at local shops, and the North End is the perfect place for Italian cuisine during the parade. 

3. Head of the Charles Regatta

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The Head of the Charles Regatta (known as the HOCR), is the largest 2-day regatta in the world with over 11000 athletes, 1900 boats, and 61 events. It is a rowing head race held on Charles River in Boston. You can watch and enjoy the event from various spectacular spots like the Eliot Bridge Enclosure or at the Reunion Village for some team spirit. The fun of the event is not limited to spectating only, you can indulge in various other sights like The Weld Exhibition, The Rowing & Fitness Expo, etc. This event is a good sight to experience Boston in October.

4. Fall Foliage Cruise

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Boston in October brings vibrant colors of fall to the scenery of the city. You can either take a walking tour or better yet, take a brunch or lunch cruise aboard the Northern Lights. You’ll have a wonderful time across the New England coast with hot cider, good food, and snuggling in a blanket. You can even have small parties on the yacht with pre-booking. The Fall Foliage Cruise typically lasts up to two hours, depending upon your booking. 

5. Fort Point Open Studio

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 Fort Point Open Studios is a program organized by FPAC artists. It takes place over a weekend in October and is met by special displays by various artists. Visitors can view and meet artists in a live studio presentation and even buy some good pieces. The program is also accompanied by music, demonstrations, performances, public art installations, and children’s art-making activities. 

6. Boston Book Festival

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Boston Book Festival is one of the biggest book festivals in the United States. It lasts for 2 days and is filled with events, books, and entertainment. This literary festival invites over 150 renowned writers, scholars, National Book Award, and Pulitzer Prize winners for presentations and discussions about anything and everything. There are hundreds of books, sessions for writers, exhibitions, along with live music, food, and various activities for children. This festival is free to attend, so make sure you don’t miss it!
Address: 32R Essex St, Suite 5, Cambridge, MA 02139

7. Boston Sports Events

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 Boston in October is a hub of sports and game spirit all over the city. You can catch games of the 5 major sports teams, namely Boston Red Sox (MLB), Boston Bruins (NHL), Boston Celtics (NBA), New England Patriots (NFL), and New England Revolution (MLS). Make sure to check out their schedule of games to get into the Boston vibes.

Amazing Halloween Places in Boston in October

October is incomplete without Halloween vibes. Boston has a lot of opportunities to enjoy this festival with costumes, stories, and candies. Check out these places to enjoy Halloween at its finest:

8. Vintage Costumes

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 You can’t enjoy any Halloween activities without a cool costume. Boston has plenty of vintage stores and outlets for crazy different and interesting outfits. You can shop from premium stores or thrift stores- the choice is yours. Here are some places you can check out: 
1. Vivan Vintage
Address: 318 Lincoln St, Allston, MA 02134
Timings: 11 AM to 6 PM

2. Bobby from Boston
Address: 545 Washington St, Lynn, MA 01901
Timings: 11 AM to 4 PMSoWa

3. Vintage Market
Address: 450 Harrison Ave, Boston, MA 02118
Timings: 11 AM to4 PM

4. Raspberry Beret 
Address: 2302 Massachusetts Ave, Cambridge, MA 02138
Timings: 12 PM to 6 PM

9. Pumpkin-picking in Boston

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 Pumpkin picking is a big Halloween tradition in Boston. There are a lot of different places to go to pick out the best ones and start the Halloween fun by carving some pumpkins. The locations for pumpkin picking are situated in the suburbs of Boston, so you can hire a cab or rent your car for a beautiful drive in the country. Here are some places you can go to:
1. Shelburne Farm 
Address: 106 W Acton Rd, Stow, MA 01775
Timings: 9 AM to 5 PM

2. Boston Hill Farm
Address: 1370 Turnpike St, North Andover, MA 01845
Timings: 9 AM to 5 PM

3. Hanson’s Farm
Address: 20 Nixon Rd, Framingham, MA 01701
Timings: 9 AM to 6 PM

4. Tougas Family Farm
Address: 234 Ball St, Northborough, MA 01532
Timings: 10 AM to 5.30 AM

10. Ghosts and Gravestones Trolley Tour

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 The Ghosts and Gravestones Tour is the perfect way to explore the spooky side of Boston. It’s a 90-minute tour that takes you through the haunted stories and two prime graveyards of the city, accompanied by tales of the same. You’ll hear about the mysterious North End troubles, the Boston strangler, the execution on the Boston Common, and much more. There is also a mention of paranormal activity at the Omni Parker House. This tour books up very quickly, so make sure to book your tickets beforehand. 

11. Halloween Movies and Shows

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Halloween invites a lot of movies and shows in Boston, all the theatres put on a horror and fun show to relive the Halloween spirit. The Coolidge theatre organizes a Halloween show every year performed by local artists. You can also attend film festivals in Boston, tickets to which can be booked online. The American Repertory Theatre puts on live music shows, theatre acts, and horror movies in the spirit of Halloween. 

12. Halloween Candy

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What’s Halloween without candies? Boston, especially in October, is a hub to get delicious treats from the market. You merely need to know where to go. Check out the following places for some unique pairings and chocolates:
1. Cacao Nuts and Chocolates
Address: 660 Centre St, Boston, MA 02130
Timings: 11 AM to 7 PM

2. Gâté Comme des Filles
Address: 1 Bow Market Way #8, Somerville, MA 02143
Timings: 12 PM to 8 PM

3. L.A. Burdick Chocolates
Address: 220 Clarendon St, Boston, MA 02116
Timings: 8 AM to 8 PM

4. Taza Chocolate Factory Store
Address: 561 Windsor St, Somerville, MA 02143
Timings: 10 AM to 10 PM

13. Prudential Center

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 The Prudential Center holds a charity and fun event called PRU BOO! for an entire day. This event is perfect for kids, including a lot of shopping opportunities in the stores on discounts. The center also organizes magic shows, face painting stalls, and concerts for kids. You can dress up and spend a fun Halloween day at the Prudential Center- all proceeds for charity. 

Boston in October is incomplete without Halloween. Apart from the above-mentioned things, you can also enjoy treats at Honeycomb Creamery,  orange wine dinner at Talulla, Halloween party at The Porch, Cheese, Candy and Wine pairings at Fleming’s Prime Steakhouse or Curds & Co, and much more! 

Beautiful Walking Tours in Boston in October

To experience the true culture of the city, you need to experience a walking tour around Boston. October is the perfect month to do so since the weather is perfect for a walk, the leaves set a good scenery, and the city has plenty of energy. You can take up any of the below-mentioned tours. 

14.  Fall Foliage Tour

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 October brings in a beautiful plethora of orange and yellow leaves, and with it, plenty of opportunities for spectacular sceneries. The tours are facilitated by a guide and driver around the city. You can simply sit back, relax, enjoy and take as many aesthetic photos as you can. You will go around New England’s countryside, farms, taverns, orchards, and much more. These tours can be booked through your hotel or personally as well. 

15. Freedom Trail Walking Tour

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 The Freedom Trail is a 2.5-mile red line, consisting of 16 significant sites of the American Revolutionary War. This tour takes you to the history of the city during the war with its collection of museums, churches, burial grounds, meeting houses, etc. This tour is offered by a lot of different setups, the official being the Freedom Trail Foundation tour. You can also walk it on your own by using a guide and spending time at places you like. 
Foundation Address: 204 Freedom Trail, Boston, MA 02113

16. Beacon Hill Crime Tour

Beacon Hill is one of the most prominent and pretty places in Boston. This tour, however, will take you on a gruesome (yet, fascinating) journey of the Boston Strangler who was the city’s most notorious serial killer. Make sure you’re comfortable with graphic information and sites before booking this ride.
Cost: The tour is free of cost and is not allowed for children below the age of 16.
Address: Tour starts at the Park St. T Station
Duration: 2 hours

Best Theatre and Music Shows in Boston in October

Boston is a city of artists and accolades in the theatre and music industry. Great artists perform in the city all year round, and October is no exception. Concerts, plays, shows- this city has it all. Make sure you check the schedule of performances during your stay. The Theatre District of Boston has some great places to look out for!

17. Wilbur Theatre

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Wilbur Theater provides a historic stage for a myriad of comedy shows and music acts. It hosts concerts almost every night, and the old-theatre-brick vibes of this place are immaculate. Make sure to check out this theatre for music-related events.
Address: 246 Tremont St, Boston, MA 02116

18. Wang Theatre

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Wang Theatre is a 3700-seat concert hall with a gold interior and a big chandelier. It is the largest performance space in the Theatre District and hosts big extravaganzas like theatre shows, ballets, music shows- all in a lavish and lush setting. 
Address: 270 Tremont St, Boston, MA 02116

19. Boston Opera House

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 The Boston Opera House seats up to 2700 people and is a premium space for Broadway musicals, concerts, and theatre productions all year round. It is embellished with gold and crystal decorations, alongside a dome ceiling. 
Address: 539 Washington St, Boston, MA 02111

20. Emerson Colonial Theatre

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Emerson Colonial Theatre has been a home for famous Broadway shows such as Oklahoma! and The Diary of Anne Frank. It seats up to 1700 people and is the oldest operating theatre in this district, along with being a Boston landmark. 
Address: 106 Boylston St, Boston, MA 02116

Other Things to Do in Boston in October

If you’d like to explore Boston on your own, here are some other things you can try in the city:

21. Back Bay

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Boston’s Back Bay is the elite and wealthy part of the city. It has brownstones and tree-lined streets, along with Victorian homes dating back to the 19th century. You can take a stroll along this path, shop in lavish stores, and relish delicacies in some true high-end restaurants. 

22. Boston Common

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 While this park is a part of the Freedom Trail tour, it is also a good place to sit and relax on a cool October afternoon in Boston. It is one of the oldest parks in the city and is spread over 50 acres. There is also a Frog Pond nearby, which makes up the perfect picnic spot. 
Address: 139 Tremont St, Boston, MA 02111
Timings: 5 AM to 11 PM

23. Castle Island

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 Castle Island is the area on the shore of the Boston Harbour, forming a part of South Boston. It is technically not an island since it is connected to the mainland. Castle Island has tons of scenic beauty, overlooking the harbor, and a beach to chill and relax. You can visit Fort Independence, visit the playground for kids, swim and have a picnic on Pleasure Bay Beach, and spend the entire day with beautiful sceneries and good vibes.

24. New England Aquarium

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The New England Aquarium is one of the best aquariums in the state. It’s not only a sightseeing opportunity for visitors, but it is also a proud catalyst for global change and the preservation of oceans. The aquarium itself is very diverse. They have thousands of aquatic animals, ranging from fur seals to giant octopus to African penguins. 
Address: 1 Central Wharf, Boston, MA 02110
Timings: 10 AM to 5 PM

25. North End

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 The North End of Boston is the ‘Little Italy’ of the city. This neighborhood in itself is a pretty place to enjoy. With little Italian cafes and restaurants, this city is a maze of narrow streets and Italian culture. It also has some sights from the Freedom Trail and is filled with Italian eateries on Hanover Street. 

Tips to Remember While Visiting Boston in October

Here are some much-needed tips to enjoy the city with the least inconvenience:
  • Boston is best explored on foot. Only rent a car if you’re going to the countryside and pack good walking shoes while enjoying the city.
  • The city offers a lot of free opportunities to attend- ranging from walking tours to exhibitions- keep an eye out for those. 
  • f you’re staying for over a week, you can get a seven-day T-card or Charlie Card to get around the subway station of the city.
  • Free Tours by Foot and Strawberry Tours offer free walking tours every day.
  • You can save money on food by eating street foods and dining in cheap restaurants- without sacrificing the quality (Check out Quincy Market). Since Boston is a college town, these are pretty decent options. 
  • You can also invest in Boston CityPass that will allow you to visit most paid museums and other attractions.
  •  If you like cycling, you can also hire a bicycle for touring the city on your own and on a budget. 

Boston in October is the most ideal way to relax and enjoy fall. There is nothing that this city doesn’t offer a tourist- especially if you know what to do. Boston must be on your list while visiting big neighboring cities!

This post was published by Pranjali Jain

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