Things to Do in Boston in October 2019

Boston Discovery Guide's recommendations for the 10 best things to do in Boston in October share a common theme:  Soak in the gorgeous October weather, enjoy gold and crimson fall foliage, and join the seasonal celebrations and festivals happening in Boston this month.

Boston's huge Columbus Day Parade, art festivals and open studios, the world-famous Head of the Charles Regatta, interesting walking tours, and New England Patriots football games give you plenty of great excuses to be outside. 

And don't forget Halloween events in Boston and nearby Salem all month!

Need more suggestions about what to do in Boston in October?  Check the October Events Calendar.

10 Top Things to Do in Boston in October

1. Watch Boston's Columbus Day Parade

Marching through Boston's North End neighborhood in odd-numbered years (2019, 2021, 2023) and East Boston during even-numbered years ( 2020, 2022, 2024), the Columbus Day Parade celebrates the city's Italian heritage, the armed forces and their contributions to American freedom, and implicitly, the voyages and explorations made by Christopher Columbus. 

This 2-hour parade attracts more people from the neighborhood than tourists, and chatting with all the neighbors and other groups while watching the bands, military units and honorary militias, floats, performers, clowns, and even antique cars march by adds to the fun. 

Be sure to:  Go for dinner in one of the mouth-watering North End or East Boston Italian restaurants after the parade: 

• North End - You'll find dozens of great choices along and near Hanover and Salem Streets - basically, you'll be happy with whatever you choose if you like Italian cuisine; if not, head to Neptune Oyster (63 Salem St)
• East Boston - Head to Santarpio's Pizza (113 Chelsea St or Belle Isle Seafood (1267 Saratoga St); you'll also find lots of good Central American restaurants along Bennington Street.

More about the Columbus Day Parade

Other Columbus Day Events

Other October Events in Boston

2.  Celebrate Halloween!

With its many historic graveyards, ghost stories, and grisly murders (think Jack the Ripper), not to speak of millions of pumpkins from the surrounding New England countryside, Boston revels in Halloween, with celebrations and special events going on all month.  If you're visiting, not-to-be-missed events are the famous Ghosts and Gravestones tours, ImprovBoston's very funny and totally outrageous GoreFest production, and if you have time, a day trip to Salem, the witch capital of the world.

• More about the Ghosts and Gravestones tour
• More about Halloween events in Boston
• More about Halloween in Salem

Check out half-price (and discount) tickets to Halloween events and shows from Goldstar:

Save BIG on half-price & discount Halloween event tickets from Goldstar

• Sinners & Saints Halloween Cruise @ MV Provincetown II (Boston) - Goldstar $20, Full price, $40
• Trick or Treat Halloween Costume Ball @ Garage Boston - Goldstar $8, Full price, $15
• Scared Stiff Halloween @ The Kinsale - Goldstar $22, Full price, $35
• Frankenstein @ Central Square Theatre, Cambridge- Goldstar $20-$30, Full price $44-$59
• Fenway Halloween Pub Crawl - Cheeky Monkey Brewing Co - Goldstar $0-$6; Full price $12
• Cirque of the Dead - Oberon - Goldstar $18-$36; Full price $30-$50
• 3-Day HalloWeek Bar Crawl - Hard Rock Cafe - Goldstar $0-$9; Full price $20
• Ghost Tour in Harvard Square @ Harvard Square, Cambridge - Goldstar $0-$12, Full price $12-$20
• Titanic Masquerade - Spirit of Boston - Full price $25, Goldstar $10
• The Sleepy Hollow Experience @ Old Sturbridge Village - Full price $18, Goldstar $35
• Harry Houdini Halloween Happening - Regent Theatre, Arlington - Goldstar $0 - $11, Full price $18
• See All Halloween Events & Shows in and near Boston

3.  Explore Boston by Bike

Another fun thing to do is to join a bike tour led by Urban Aventours (109 Atlantic Ave, just across from Christopher Columbus Park in Boston's North End).  Tours depart several times daily, and you can select from a bunch of interesting options, including fall foliage tours. 

Find out more about Boston Bike Tours

4.  Watch the Head of the Charles Regatta

Sculls (racing boats) powered by rowers ply the Charles River almost year-round - truly a quintessential Boston sight. 

But when over 8,000 local and elite rowers from around the world gather for the huge Head of the Charles Regatta in late October, they fill the river with an exciting spectacle that attracts huge crowds along the banks and looking down from the bridges. 

Best of all, the Regatta gives you the perfect excuse to be outdoors enjoying fall foliage during the most beautiful season of the year. 

Find a great viewing spot from either the Cambridge or Boston side of the river or one of the bridges, and enjoy the races!

More about the Head of the Charles Regatta

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Find out more about Boston discount cards, and how they give you big savings on top attractions.

5.  Join a Walking Tour

Combine walking around and viewing Boston's fall foliage with seeing interesting parts of the city from an "insider" perspective by taking a walking tour.  Here are 4 excellent choices:

• Boston Movie Mile Tour - Fascinating walking tour through Beacon Hill, where you'll see 30+ sites featured in movies and TV shows, and hear the fascinating behind-the-scenes details from the tour guides, all of whom are actors.  A 3-hour bus tour option is a great choice for rainy days. 
  More about the Boston Movie Mile tour and ticket information
• Boston Chocolate Tour - Offered for several neighborhoods including Beacon Hill, Back Bay, the South End, and Cambridge's Harvard Square.  Plenty of chances to sample chocolates along the way.  Definitely Boston's sweetest tour!  
  More about the Boston Chocolate Tour and ticket information
• Boston Wine Tasting and Walking Tour - You'll stroll around one of Boston's iconic neighborhoods - the North End, South End, Back Bay, or Harvard Square - while your guide leads you to 3 award-winning restaurants where you'll sip up to 6 different wines while your guide shares information about Boston's culinary scene, wine pairings, and other tips.  Boston in October doesn't get much better than this! 
  Find out more and book your tour now
• Fenway Park Tour - This popular tour takes you right out on the field, up into the Green Monster, and behind the stands at Fenway Park.  Lots of fascinating Red Sox lore. 
  Find out more

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More Top Tours for October

6.  Indulge Your Passion for Sports

For Boston sports fans, October offers Bruins, Celtics, and Patriots games.  With TD Garden and Fenway Park right in the middle of the city, getting to a game couldn't be easier.  Even though Gillette Stadium requires a little more time to reach, you can easily get there and back on the special "Patriot Train" departing from North Station.

• Boston Bruins Schedule
• New England Patriots Schedule
• Boston Celtics Schedule

7.  Visit Open Art Studios

The Fort Point Arts Community, located next to the Fort Point Channel, dividing Downtown Boston from the South Boston Waterfront, has flourished since the first artist pioneers arrived in the 1970s to convert abandoned factories to art studios and galleries.  More than 300 artists now live and work there, and on one special weekend in October and another in May, open their studios to the public in one of the city's biggest art events. 

Fort Point Open Studios provide a wonderful opportunity to explore the many diverse studios, talk with the artists, and immerse yourself in this world of art.  It's also a great excuse to explore more of the rapidly developing South Boston Waterfront.

Get dates and times for the Open Studios from the October Events Calendar

Find out about the Fort Point neighborhood's top chef-owned restaurants

8.  Photograph Boston's Gorgeous Fall Foliage

By early October, Boston's many trees begin to show tinges of gold and crimson and by the end of the month, breathtaking fall foliage can be seen throughout the city.

October is the easiest time of the year to take stunning photos. You'll see plenty of tourists and locals walking around the city with cameras in hand.

If you have to pick just one spot for your foliage viewing/photographing, head to the Lagoon in Boston's Public Garden.  With giant weeping willow trees and bright-colored maples of many species reflecting in the water, you can take stunning photos from many different perspectives. 

Be sure to check the views from the middle of the suspension bridge - or stand on the shore and make it the focal point of your photos.  As an added benefit, Boston's famed swans will still be in residence for most of the month.

Want to combine foliage, sightseeing, and photography?  Join a Boston Photography Tour of nearby historic Beacon Hill

9.  Enjoy a Concert or Comedy Show

With all the Boston and Cambridge college students back in town, you'll find plenty of entertainment to choose from every night:    

Valentine's Day Special Promos (good through 2/14)

     TicketLiquidator - Enter VDAY15 to get $15 off orders of $150+
     TicketNetwork - Enter VDAYTN to get $15 off orders of $150+

Ticket Discount Codes

     TicketLiquidator - Enter WINTERTL to get $10 off orders of $250+
     TicketNetwork - Enter TNTIX to get $10 off orders of $300+

Check Boston Discovery Guide's Concert Schedule for October for more ideas.

10.  Bask in the Warmth of the Sun

In just another month, October's relatively warm, sunny days will be just a memory  - so go outdoors and soak up the sunshine now! 

Some suggestions:

• Patio dining at Boston restaurants - You can still comfortably dine outdoors this month, especially if you're wearing a sweater
• Picnic on the Rose Kennedy Greenway.  Need something to eat?  Walk over to the Boston Public Market, where you'll find plenty of tasty take-out.  More about the Greenway
• Explore a neighborhood - Beacon Hill, across from Boston Common and the Public Garden offers plenty of breathtaking 18th and 19th century architecture. 
• Relax on the Esplanade - Boston's Esplanade along the Charles River offers spectacular scenery from wharfs floating just above the water - Find a chair, relax, and enjoy fall foliage along the shore.  More about the Esplanade

More to Do in Boston in October

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More to See and Do in Boston during October

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Save with Discount Tickets

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• Saint Paddy's Green Electric Yacht Party - @ Spirit of Boston - Goldstar $10-$13, full price $20-25
• Snow Tubing & Brewery Adventure - Goldstar $72, full price $99
• The Runaway Bunny @ Boston Center for the Arts- Goldstar $15, Full price $30
• Fifty Shades of Men @ Icon Nightclub - Goldstar $0-$13, Full price $25
• Ski & Snowboard Crotched Mountain: Roundtrip bus, rentals, lift ticket - Goldstar $87; Full price $125
• Live Music @ City Winery - Goldstar $10-$25; Full price $22-$50
• Tipsy Chocolate Tours - Boozy walking tour in Boston's Back Bay - Goldstar $48; Full price $68
• Huzzah! Tavern Nights - Boston Tea Party Ships & Museum - Goldstar $41; Full price $55
• History Comes Alive! - Boston Tea Party Ships & Museum - Goldstar $19; Full price $30
• Stand-Up Top Stars & Rising Comedians - Nick's Comedy Stop - Goldstar $0-$10, Regular $20
• Riot Improv Mainstage: Your Quirky Family - Rozzie Square Theatre - Goldstar $8, Regular $15
• Riot Improv: Mashup with MassMouth - Rozzie Square Theatre - Goldstar $8, Regular $15
• Stand-Up at the Comedy Scene - Patriot Place (across from Gillette Stadium) Foxboro, MA - Goldstar $10, Regular $20

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Check Out More Top Boston Events Each Month

January   |   February   |     March  |  April   |    May    |    June   |   July   |    August   |    September  |  October   |    November   |    December  |  Year at a Glance 

More Recommendations for You

• Halloween Events in Boston
• Halloween Events in Salem
• Top Things to Do in Boston during November
• Best Ski Slopes near Boston
• Christmas in Boston

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