J.J. Donovan’s
The starting line. Optimism is high. Hydration choices are already questionable.
Cheers
Touristy? Sure. Iconic? Absolutely. Sometimes obvious stops are obvious for a reason.
Cask ’n Flagon
The Fenway checkpoint. Bonus points if there’s a game and the city tries to trap you.
The Sevens
A proper Boston bar stop. Small, classic, and exactly the right kind of questionable.
The Bell in Hand
Old, historic, and somehow still willing to let people like us through the door.
Warren Tavern
History, beer, and the growing realization that this route is not getting shorter.
J.J. Foley’s
The mood-check stop. Every course needs one place that tests the spirit.
Harpoon
A brewery stop, a reset point, and a reminder that food planning matters.
Biddy Early’s
If you make it here, strangers may start recognizing your poor decisions in public.
Sullivan’s Tap
Late-course energy. Feet hurt. Spirits weirdly improve. Nobody knows why.
Trillium
The finish line. Redemption, relief, and maybe one more beer because apparently lessons were not learned.