Sure, ClioCon is the main event, but why let the fun stop there? Boston’s got a ton of activities that’ll turn your conference trip into an all-around adventure. From spooky tours to brew-fueled days, here’s how to pack in some extra fun while you’re in town.
FOR THE AESTHETIC EXPLORER
Boston in October is peak cozy-core. After soaking up big ideas at ClioCon, slow it down with a scenic stroll through Boston Common and the Public Garden—two of the city’s most photogenic spots. Snap that perfect leaf-crunching Boomerang, or just take it all in IRL. Want more? Rent a car and head west to the Berkshires or north to New Hampshire for an explosion of fall color that practically demands a flannel selfie.
FOR THE SPOOKY SEASON LOYALIST
Into haunted history, candlelit graveyards, and vintage vampire vibes? October in Boston thrives in the spooky department. Just a 30-minute train ride away, Salem is Halloween HQ with its witch trials lore, ghost tours, haunted happenings, and full-blown festivals. Go for the haunted house, stay for the cauldron cocktails. Trust us—it’s a scream.
FOR THE FALL FEST FANATIC
Fall in Boston = brewery season. Local favorites like Harpoon and Sam Adams go all out with Oktoberfest events packed with live music, pretzels, and—obviously—seasonal brews. And if you want to mix in a little culture with your cider, the world-famous Head of the Charles Regatta hits the Charles River the Saturday after ClioCon. Think elite rowing teams, riverside food trucks, and a very fun international crowd.
FOR THE HISTORY BUFF ON THE MOVE
Boston’s crisp fall air (50s–60s °F) is perfect for walking off your ClioCon buzz. Whether you’re meandering through the Freedom Trail, soaking up the history of Beacon Hill, or wandering around Harvard Yard, you’ll love the crisp sweater weather while you get your steps in and take in the city’s charm.
FOR THE SEASONAL SNACKER
If you live for fall flavors, Boston’s got your cravings covered. We’re talking hot apple cider, cider donuts, lobster mac, and clam chowder in a bread bowl that basically hugs your soul. Hit up a cozy North End trattoria for pasta, or try a farm-to-table spot that leans hard into seasonal menus. This is not a city that skimps on flavor—or comfort food.
FOR THE ART & CULTURE CONNOISSEUR
Fall is Boston’s cultural comeback season. Post-conference, swap panels for playbills: catch a Broadway show at the Boston Opera House, see a world-class performance from the Boston Symphony Orchestra, or explore galleries at the MFA and Isabella Stewart Gardner Museum. Whether you’re into fine art or fringe theater, the city’s creative scene delivers.
FOR THE SOX-AND-CELTS DIEHARD
If you bleed team colors, Boston’s the place. Catch the Red Sox at iconic Fenway Park (yes, they still sell peanuts and Cracker Jack), watch the Bruins or Celtics kick off their seasons, or road trip to Foxborough for a Patriots game. Pro tip: even if you don’t snag game-day tickets, post up at a sports bar with diehards. The energy is electric.
With ClioCon and Boston’s endless attractions, this trip is shaping up to be one for the books. Conference wisdom, fall fun, and a whole lot of adventure—what could be better?