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Guided Ride · Easy
Wednesday, October 21, 2026 · 6 PM – 8 PM
Wednesday Night Flex Walk
4.3 miles
FreeWomen and nonbinaryBeginner-friendly
Boston Women over 40 Walking Group
**In the Steps of Whitey Bulger** — we're moving on to a more recent historical chapter in Boston — walking the parts of **Southie** that were once controlled by the infamous Whitey Bulger and his mob gang. I cannot emphasize enough that this is not meant to be a voyeuristic stroll through the world of mobsters, but simply to allow us to experience one of the many neighborhoods of our amazing and diverse city, through a particular lens in time.
We will, however, have some wonderful stories to tie in to the walk and we are lucky to have **Janet** join us, whose knowledge of (and infectious enthusiasm for) Boston history will make this walk one to remember.
In order to cover more ground, we will meet just outside the main, arched entrance to the **John Joseph Moakley U.S. Courthouse**.
*Note*: even though the official address is 1 Courhouse Way, the entrance is on **Northern Av., near the corner of Courhouse Way**. From there, we will pass through Pier 4, as we make our way to Southie, where we'll explore the neighborhood, including a stop for refreshments at the **L Street Tavern** (from Good Will Hunting), and end at the **Broadway Station**.
This walk is approximately 4.3 miles/1.5 hours,
Looking forward to a great walk, full of history, intrigue, and fun!
Blair
\*\*Liability Release - AS A CONDITION OF ATTENDING THIS MEETUP, YOU AGREE TO hold harmless, and indemnify the organizer and her heirs, and all members and participants of this Meetup group from any and all claims for injury, illness, death, and/or property damage including those caused by negligence, ignorance, inexperience and other reasons. You also agree to assume all mental, physical, financial, and/or other risk associated with this meetup. All meetup activities pose inherent risks and dangers. Participation in these activities is voluntary and dependent upon your own personal judgment.
Date
Wednesday, October 21, 2026
Time
6 PM – 8 PM
Where
John Joseph Moakley United States Courthouse, 1 Courthouse Way, Boston, MA 02210
Organizer
Boston Women over 40 Walking Group