23. Northampton, MA
Must-eat/drink: Ice cream from Herrell's, craft beer at The Dirty Truth
Don't leave without: Hiking to the top of Mount Tom or Mount Holyoke for stunning views of the Pioneer Valley; seeing a show at the historic Calvin Theatre (opened 1924)
Weekend highlights: If you didn't know any better, you might mistake this artsy enclave on the Connecticut River with any big city square in Cambridge or Boston. It's less quaint Western Mass town and more edgy urban oasis/cultural center, with all the bars, galleries, and hipsters to prove it. A get-yourself-acquainted stroll should include the iconic/quirky Faces gift shop, Ben & Bill's Chocolate Emporium, Broadside Books, Thornes (there's a mall hidden behind those doors!), and the aforementioned Herrell's for a scoop of ice cream.
But at this point, you're really just getting started. Rent a bike and hit 150-acre Look Park, stroll through Smith College's Botanic Garden and Museum of Art, and ride the 11-mile Norwottuck Rail Trail over to nearby Amherst (UMass). Absolutely stop for a beer on the roof deck at the Northampton Brewery and/or play a game of Space Invaders at Quarters, a bar located along the trail in Hadley.
And speaking of bars and food and nightlife, there are too many options for one weekend so just jot these recommendations down: breakfast at Sylvester's, burgers at Local, pizza at Joe's, seafood at Eastside, coffee at The Roost, and cannoli at La Fiorentina. Your obligatory night-out bar crawl should touch The Green Room, The Dirty Truth, and McLadden's, which pours 105 draft beers and 160 whiskeys. Depending on your age/intentions, you might end at Tunnel Bar, a hip lounge/martini den built into -- you guessed it -- an old tunnel under the railroad tracks. Northampton's also a hotbed of live tunes with a solid ensemble of venues (the Calvin Theatre, Iron Horse Music Hall, Academy of Music); a lot of bands pass through town so if that's your jam, see who's playing here.
And finally, you don't come to Western Mass to sit inside, so spend a day exploring the surrounding area. Hike/drive up to the Summit House on Mount Holyoke; appreciate the farms (corn! Asparagus! Dairy!) as you drive along the Route 47 Scenic Byway toward South Hadley (just be sure to grab a coffee at the Thirsty Mind when you get there); or, if you're up for venturing a little further from home, visit the insanely popular Tree House Brewing Co. in Monson or hop on the Mohawk Trail (Route 2) out to the Berkshires and North Adams, Mount Greylock, and MASS MoCA (Massachusetts Museum of Contemporary Art). There is no more gorgeous drive to peep the fall foliage in all of the country. -- Dave Baldwin, Travel editor