- Go mini-golfing at Baker's Golf (Rt. 7, wicked fun!)
- Eat delicious ice cream at Jilly's, on Elm Street
- Fulfill your Jury Duty obligation
- Try to find places to park
- Go around the main circle 'til people start to get suspicious. And then do it again.
- Ben & Jerry's
- Elizabeth's
- Get a tattoo
- Get a piercing
- Get hit on by sketchy old men on North Street (townie summer-pastime!)
- Visit Ricardo
- Sail on Pontoosuc, or Onota. 'Cause Pittsfield is so cool it has 2 lakes.
- Go to the Berkshire Museum (South Street)
- Ski at Bosquet's, or go downhill racing and play on the waterslide in the summer!
- Zucchini's
- Ski Fanatics
- Berkshire Hills Country Club
- Pittsfield Country Club (swanky)
- Home Depot, Wal-Mart, and Michael's, but Michael's is kinda expensive, so JoAnne's