Ashmont After Hours Event

Spend a cozy October evening out in the neighborhood with Ashmont After Hours, where you can enjoy live music, art, and delicious food all in Peabody Square.

7:30 pm – Meet at The Local Hand for pumpkin painting and a special 1-hour flash sale

8:30 pm – Head over to Tavolo for dinner, drinks, music, and more fun featuring a DJ set courtesy of @unnoaaro

Your ticket includes:

– a seasonal cocktail
– a drink of your choice at Tavolo
– dinner at Tavolo
– all supplies for the pumpkin painting

Spaced is limited – reserve your tickets early here! 

Boston Fire Aerial Drill Team Exhibition + Open House

You’ll have several opportunities to check out the Boston Fire Aerial Drill team this week!  On Monday, they will be performing at City Hall Plaza at 12pm, Ellis School in Roxbury on Tuesday at 11:30am, on Wednesday at the Umana Barnes Middle School in Eastie at 10:30 am, Holy Name on Thursday at 9am, Friday at the Mathers School in Dorchester at 12pm and on Saturday, at Castle Island at 12pm, since as early as the 1930s, the Aerial Exhibition Drill Team has demonstrated the skills and capabilities of the Boston Fire Department during Fire Prevention Week. You can learn more here. 

As part of Fire Prevention week, BFD will host an open house on Saturday, October 11th from 10am-2pm at Engine 17, Ladder 7 – 14 Winter Street in Dorchester (Meeting House Hill) where you can meet your neighborhood firefighters, explore fire trucks and gear, walk-through fire safety bound house, learn lifesaving skills and fire safety tips.  Plus giveaways and free hot dogs and hamburgers!

Adams Village Fall Festival – POSTPONED until Saturday, October 18th

On Sunday, October 12th, from 12–5 PM, enjoy a day full of fun in the heart of Adams Village!

✨ Shop and support local businesses & vendors
✨ Enjoy bites from amazing local restaurants
✨ Kid-friendly activities + face painting
✨ Music, raffles, and get your picture taken by a photographer at our fall-themed photo booth

This event is organized by Fringe Boutique and Everything Adams Village!

New and Improved Walsh Park

Last week, Mayor Michelle Wu joined Interim Boston Parks Commissioner Cathy Baker-Eclipse, elected officials, and the Lower Mills community to cut the ribbon on improvements to Walsh Playground in Dorchester. The celebration marks the completion of a $4 million renovation, funded in the City’s five-year Capital Plan, to revitalize the park. This includes new play equipment, a splash pad, revitalized tennis and basketball courts, upgraded playing fields, and community areas.  You can get all the details here.  Stop by and check it out this weekend!

Live Music at McGonagle’s

Enjoy Dalton and the Sheriffs Solo Acoustic Show at McGonagle’s on Sunday night at 8pm! Stop by for dinner and stick around for the entertainment!

Participate in Boston Firefighters 10K

The 43rd Annual Boston Firefighters 10K Road Race returns to Dorchester and Florian Hall on October 12, 2025, at 9am! The annual event brings together participants from all walks of life to celebrate fitness, camaraderie, and support for the brave men and women of the Boston Fire Department. Held against the backdrop of the historic city, this race offers a scenic and challenging course that winds through Dorchester.  Get all the details here! 

Book your holiday appointments at BostonX

October is the perfect time to plan ahead for the busy holiday season with BostonX!  With calendars filling up quickly, now is the moment to secure your appointment and make sure your treatments are timed perfectly. Whether it’s a refreshed complexion, smooth skin, or subtle enhancements, booking early ensures you’ll look and feel your best for every gathering, photo, and celebration this season brings – book your spot here! 

Participate in Open Streets in Mattapan on Saturday

Open Streets Boston’s 2025 series continues with the City of Boston’s next event in Mattapan – a brand new neighborhood for this year! On Saturday, October 18, we’ll be transforming Blue Hill Avenue into a pedestrian-only space that’s safe and open for everyone to explore and enjoy.

This is your opportunity to experience Mattapan like never before with a lineup of FREE activities, live entertainment, delicious food vendors, and much more. Connect with your community, make new friends, and experience this vibrant neighborhood in a completely new way.  Get all the details here! 

$5 Ferry Rides

Celebrate the closing of the 2025 public ferry season with a $5 trip to Spectacle Island or Peddocks Island from Saturday, Oct 11 to Monday, Oct 13!  Tickets are now available online to reserve and purchase. Tickets purchased in-person are first come, first serve, so we recommend purchasing in advance! Learn more here! 

Weekend Fun at Yellow Door

Spend your weekend at Yellow Door featuring tacos, margaritas, weekend brunch (Saturday + Sunday) and $1 oysters on Sunday!

Explore Boston’s Stunning Fall Foliage

Who says you need to leave the city to see beautiful foliage? Did you know that the Emerald Necklace is home to more than 8,000 trees, and each autumn, they work together to put on a show? Follow the FREE Emerald Necklace Foliage online tour that showcases some of Boston’s best leaf-peeping and unique sights along Frederick Law Olmsted’s Emerald Necklace parks. It is a great tool to use as a guide when touring the park system. Also, according to the Emerald Necklace Conservancy team, their preferred spots for leaf peeping in the Necklace are Jamaica Pond, Franklin Park’s Scarboro Pond, and Schoolmaster Hill in Franklin Park since the elevation affords a lovely sweeping vista. Simply follow this link to start the FREE online tour!

SPORTS!

Patriots vs. Saints –Sunday, October 12th at 1pm.

Bruins vs. Sabres – Saturday, October 11th at 7pm

MLB Playoffs – check out the schedule here.

If you’re watching the game this weekend, check out our list of 10 places to catch the action in Dot, or check out 12 of our favorites in South Boston!

Check back! This list may be updated