Regatta

-- The Community Sailing Program on Jamaica Pond presents a fundraiser for its annual Summer Youth Program, a chance for local kids to take sailing lessons for free. The event features sailing, a string quartet, and goodies from Blanchard's, Boston Beer Company, and Gourmet Caterers. And, it's what Our Popular Mayor will be doing tonight. Jamaica Pond, Jamaica Plain, 5 p.m. $50.

Dancing Hipsters

-- The Hearthrob dance party is the place to go if you want creepy men in trucker hats to take pictures of you while you are drunk and post them on the internet. On the other hand, beats from Dan Oh, Gina Turner, Red Foxx, Morgan Louis, and Baltimoroder might make you forget your 401(k) balance. Middlesex Lounge, 315 Mass. Ave., Cambridge, 9 p.m. $5.

The Sound of New England

-- Phantom Buffalo, the pride of Portland, Maine, brings its twee harmonies to Jamaica Plain. (Think Belle and Sebastian meeting California sunshine pop and, inexplicably, getting along.) Performing with locals Reports and the Needy Visions. Co-sponsored by Dewar's and the Weekly Dig. Milky Way Lounge, 403 Centre St., Jamaica Plain. 9 p.m. Free.

Image of Bostonist's favorite Jamaica Pond resident, the white squirrel, labeled "Bostonist" by Flickr user Steve Garfield.