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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.

  • More reasons to leave the house →

BOSTON’S FOUR-LEGGED TRAVEL EXPERT

Photo: Leia from Boston

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

Photo: Timmy Walsh

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

10.15 - JIMMY DUNN

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:

🔥 TRENDING:

My niece gets baptized this weekend and I’m the godmother praying Catholic muscle memory is a thing.