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- Daily Email - Friday - 10/9/2026
Daily Email - Friday - 10/9/2026
New England is hitting peak leaf-peeping season (say that three times fast) and four local spots were ranked among the best fall destinations in America. Wherever the foliage takes you, start with a full stomach: win $150 to The Tip Tap Room for your pre-adventure fuel.
JUST ANNOUNCED
Bill Burr, Tom Segura and Dave Chappelle in one weekend? Your plans just made themselves. Enter to win a trip for two to Fastball Comedy Festival October 17th-18th, with airfare to Phoenix, three hotel nights, two 2-Day Premium passes, festival merch and dinner for two.*
I've got a feeling we're going to be hearing the name nimino a lot more. Catch the UK producer at Roadrunner on November 6th before your friend tells you they saw him first.
Syd is stepping back into the spotlight with the Beard Tour, hitting House of Blues on December 6th. Go get lost in smooth vocals for a few hours.
Elder millennials, mark your calendars. Iliza Shlesinger is bringing the Free Nights & Weekends Tour to Chevalier Theatre next October.
BOSTON’S FOUR-LEGGED TRAVEL EXPERT
Boston pup, Leia, and her human, Brit, are the duo behind Leia From Boston, where they share dog-friendly escapes, hidden gems and local adventures. Their mission is simple: prove that traveling with your dog doesn’t have to make things harder. In fact, it might make the trip a whole lot better.

THIS WEEKEND
10.10 - FALL FEST, ADAMS VILLAGE 10.10 - VEND-O-RAMA, FIRST ST MARKET 10.10-10.11 - MARKETS FOR MAKERS, SOWA 10.11 - OPEN NEWBURY ST, BACK BAY 10.11 - TOBIN TAKEOVER, THE ANCHOR |

10.11 - NOT AFRAID TO FAIL FEST 10.15 - JIMMY DUNN 10.23 - ECHOES OF FLOYD 10.28 - CARSIE BLANTON (WIN) 11.6 - JAMANTICS |
LOCALS ONLY
One last Oktoberfest feast is in order: Mei Mei is sending off the season with a special menu of bottomless dumplings, which sounds like a challenge we’re willing to accept.
Short Path’s annual fall extravaganza takes over the distillery tomorrow. Apple Booze Bash shuts down a whole street for live music, spiked cider flights, a drag show and more.
Happy Hispanic Heritage Month! Boston’s Cuban community comes together at City Hall Plaza on Sunday for the 34th Cuban Flag Raising Ceremony.
WIN STUFF
🚨 LAST CHANCE:
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FEATURED
My niece gets baptized this weekend and I’m the godmother praying Catholic muscle memory is a thing.







