October brings crisp fall days, cozy movie nights, and plenty of ways to connect on The Greenway! From our Fall Movie Series and public art to artist talks and seasonal programming, there’s still plenty to see, do, and enjoy as the days get shorter. Read on to discover this month’s highlights and make the most of fall on The Greenway!

 

On The Greenway

Fall Movie Series: Throwback Thursdays
Presented by the Greenway Business Improvement District (BID) and the City of Boston’s Office of Tourism, Sports, and Entertainment

October 8, 15, 22, and 29 | Starting at sunset (6:30 PM) | Wharf District (Between Milk Street and India Street)
This fall, it’s all about the 90s, and we’re ringing in sweater weather with four films that are perfect for cozy autumn evenings against the city skyline. Themed candy and snacks will be available to purchase onsite as well as food from one of our food trucks. Plus, join us before each showing for a free family-friendly activity, beginning at 5:30 PM. Each week’s activity will match the theme of the movie. 

• October 8: The Parent Trap (1998)
  • Activity: Friendship Bracelets and Photo Frame Decorating
• October 15: Jumanji (1995)
  • Activity: Bird House Decorating
• October 22: 10 Things I Hate About You (1999)
  • Activity: Notebook Decorating
• October 29: Casper (1995)
  • Activity: Pumpkin Decorating

 

From Muralismo to “The Midnight Ride”
Presented by Boston 250, a public-private partnership between the City of Boston and private sector partners, including Meet Boston, State Street, The Boston Foundation, John Hancock, Eastern Bank, Liberty Mutual, Blue Cross Blue Shield of Massachusetts, Vertex Pharmaceuticals, and PNC Bank.
October 15 | 5:30 to 7:30 PM | Dewey Square
Join us to hear our 2026 Dewey Square muralist, Rixy, in conversation with projection artist Pamela Hersch. Together they’ll explore the relationship between large-scale public murals and thriving democracies. Enjoy music from DJ Oyade and live band FM Collective, grab a bite from our food trucks, and be one of the first to view the new illumination of The Midnight Ride. This event will kick off a 6-month nightly projection onto Rixy’s The Midnight Ride, bringing the mural to life in Downtown Boston. Learn more and RSVP on our Eventbrite.

From Muralismo to “The Midnight Ride” is funded by Boston 250, a public-private partnership between the City of Boston and private sector partners, including Meet Boston, State Street, The Boston Foundation, John Hancock, Eastern Bank, Liberty Mutual, Blue Cross Blue Shield of Massachusetts, Vertex Pharmaceuticals, and PNC Bank.

Support for the Dewey Square Mural projectors is generously provided by the Lynch Foundation and Laura Connors and Brian O’Connell.

 

As Long as the Sun Lasts: Vivian Tran and An Hà In Conversation
October 27 | 5:30 to 7:30 PM | Pao Arts Center
Join artists Vivian Tran and An Hà for a conversation about the artists’ individual practices as well as the work of their curatorial and arts programming collective, Copenger. The talk will be followed by a walk to Chin Park and an artist-led tour of Tran’s because you are the sun; because you are the thread on The Greenway.

 

Around The Area

STEAM Family Workshops: Marble Mazes
Hosted by Boston Children’s Museum
October 11 and 25 | 2 to 2:45 PM and 3 to 3:45 PM | Boston Children’s Museum
STEAM Family Workshops are 45-minute to one hour long, hands-on/ minds-on challenges designed to foster intergenerational learning and provide opportunities for creative thinking and expression. Space is limited; first come, first served. You can sign up in front of the STEAM Lab.

 

The Art of the Woodturner
Hosted by the Arnold Arboretum of Harvard University
October 17 and 18 | 10 AM to 4 PM | Hunnewell Building at the Arnold Arboretum
Woodturning is the art or process of fashioning wood into various forms and shapes by means of a lathe. Returning to the Arnold Arboretum for the 11th year, The Art of the Woodturner will again offer visitors the chance to see an amazing variety of woodturned pieces: large and small, functional and sculptural.Work from three New England clubs will be on view: the Association of Revolutionary Turners, Central New England Woodturners, and Massachusetts South Shore Woodturners. Each craftsperson brings their own personal artistic vision to the objects they create, and the pieces in maple, cherry, and other wood offer a unique look at the personality within the wood itself. Be sure to look for pieces turned from Arboretum wood as well. Experience in-depth demonstrations on the lathe in the Hunnewell Lecture Hall at 11:00am, 1:00pm, and 3:00pm on Saturday and Sunday, and throughout both days on the Hunnewell lawn.

 

Annual Reconfiguration of the Abstract Sculpture
Hosted by Friends of Armenian Heritage Park
October 18 | 7 AM | Armenian Heritage Park on The Greenway
A crane lifts and pulls apart the two halves of the split rhomboid dodecahedron, made of steel and aluminum, to create a new sculptural shape, symbolic of a new life. The annual reconfiguration serves as a continual source of discovery, delight and engagement, enhancing the visitor experience.

 

Love Letters LIVE: Halloween Edition with the B-Side and Rory Uphold
The Boston Public Market Association in collaboration with The Boston Globe and The B-Side
October 21 | 6 to 8 PM | Boston Public Market
Celebrate the Halloween season at BPM as we welcome Emily Schario of B-Side; Meredith Goldstein, host and writer of the Boston Globe’s Love Letters advice column and podcast; and L.A.’s Rory Uphold, writer, podcast host, and author of “A Final Girl’s Guide to the Horrors of Dating,” a hilarious memoir and guide to dealing with ghosting, zombies, and witches … and how friendship can be the best kind of magic. Head to the Hub to:

• Join a discussion with Meredith, Emily, and Rory about the dating scene and how to survive it
• Relax by partaking in seasonal crafts
• Play “Rom-Com or Horror” Trivia – for prizes
• Enjoy complimentary seasonal treats
• Take a picture with the GIANT pumpkin at BPM. It’s Instagram perfection!

Fall Fest: Run & Walk for the Esplanade
Hosted by the Esplanade Association
October 25 | 8 AM to 12:30 PM | Fiedler Field
Join the Esplanade Association on Sunday, October 25 for a morning of fitness, community, and fall fun while supporting the Esplanade Association’s mission to revitalize, enhance, sustain, and build community in one of Boston’s most treasured public spaces. Whether you’re racing the professionally timed 5K or enjoying our 1.5 mile community walk, there’s a place for everyone. The walk welcomes participants of all ages and abilities – including families, dog lovers, and anyone looking to enjoy the beautiful fall scenery on the Esplanade’s shared-use public pathways.
The fun doesn’t stop at the finish line! Stick around for Fall Fest, featuring family-friendly activities, local community partners, food, music, giveaways, seasonal fun, and NEW this year: the Paws & Pumpkins Parade, where four-legged friends can join in the celebration and partake in a festive costume contest! Whether you’re running, walking, cheering on participants, or simply enjoying the festivities, you’ll be helping support the Esplanade Association’s free programs, events, and year-round care of Boston’s iconic waterfront park.

 

Family Halloween Party & Pumpkin Stroll
Hosted by Boston Public Market
October 31 | 10 AM to 3 PM | Boston Public Market
Join us at the Boston Public Market on Saturday, October 31st for a day of seasonal fun for the whole family! We’re excited to partner again this year with the Children’s Museum, the Rose Kennedy Greenway, and the New England Aquarium for this year’s Pumpkin Stroll. Stop by the Market for some seasonal fun with FREE family-friendly activities including Halloween-themed crafts, coloring, games, and more! Then, take a stroll along the Greenway to search for colorful pumpkins, and stop by the Greenway Carousel in costume for a free ride. This is a day packed with Halloween fun and excitement – you won’t want to miss it!

 

Wicked Plants, a botanical Halloween
Hosted by Friends of Armenian Heritage Park
October 31 | 12 to 3 PM | Hunnewell Lawn at the Arnold Arboretum
On the afternoon of Halloween, stop by the Hunnewell Lawn to learn about the most sinister plants in the Arboretum’s collections. Armed with spiky thorns, sticky latex, and chemical warfare, these plant species defend themselves from hungry herbivores, other plants—and sometimes from humans who wander too close. Others try to poison their neighbors, practice explosive seed dispersal, or even glow under black light. Drop by for this family friendly event and experience Halloween, Arboretum-style.

 

Download Our Monthly Flyer

If you’re looking for family-friendly fun or an after work outing in Boston this month, we hope you’ll visit The Greenway! You can also download a PDF version of our Monthly Roundup to print or share with friends, family, or your next adventure crew.