"The Hamptons" (aka Hampshire County, MA)
Distance from Boston: 106 miles west; two-hour drive
Hampshire County, made up of Northampton, Easthampton, Southampton, and Westhampton, boasts plenty to do between them and the other hamlets dotting the countryside. Your journey begins at Ye Ol’ Watering Hole (Northampton) for regional brews and the 4,000+ beer can museum. More beer awaits in Easthampton, home of Fort Hill Brewery and Abandoned Building Brewery. Cycling enthusiasts can ride a series of connected bike trails (between Hadley, Northampton, and Easthampton), enabling you to drink all that beer and commune with nature. If you want/need more of the great outdoors, hiking the Seven Sisters (part of the Holyoke range) nets you some sweet scenery. If you forgot your bike or don’t even have one, Northampton Bicycle and Valley Bike & Ski Werks (Hadley) offer inexpensive daily ($25) and weekly ($90) rentals.