Pittsfield

Popular Trips

New York City, United States - Brooklyn, United States - New York City, United States6-Day United States AdventureRomantic Winter Escape to Pittsfield, IllinoisEnchanting Winter Romance in Pittsfield, MaineEnchanting Winter Escape in Pittsfield, VermontEnchanting Winter Escape in Pittsfield, NHEnchanting Winter Romance in Pittsfield, WisconsinShow all

Curated Itineraries

5-day trip to Pittsfield, MA5-day Foodie Adventure in PittsfieldCultural and Culinary Journey in Pittsfield, MACultural Delights and Culinary Journeys in Pittsfield, MA5-Day Driving Adventure from Columbus to the Berkshires5 Days in the Berkshires Massachusetts5-Day Adventure in Berkshire CountyShow all