What’s on for singles
Events through the year that make an easy first or second date.
Summer
A picnic on the Tanglewood lawn
Tanglewood at 297 West Street, Lenox, invites you to picnic on the lawn and bring your own food and drinks. Check the 2027 season and check prices on bso.org.
Source: Boston Symphony Orchestra: Tanglewood FAQ, checked 8 November 2026
September
The Big E
The Big E in West Springfield runs September 17 to October 3, 2027, with food and exhibits from across New England. A weekday visit is calmer.
Source: The Big E: Information, checked 8 November 2026
October
Fall views from Mount Greylock
The summit road on Mount Greylock, the state's highest point, is open from mid-May to late October. Go before it closes for a wide view over the Berkshires.
Source: Mass.gov: Mount Greylock State Reservation, checked 8 November 2026