Quiet, charming, and very Main Street, USA. There actually is a “Main Street” (well, Central Street) with most of the restaurants and shops, where you’re bound to see packs of middle-school kids in soccer uniforms and moms with double strollers. Wellesley is a WASPy, family-centric town, no doubt about it. The public schools are widely considered some of the best in the Boston area.
Don’t move to Wellesley if you’re looking for excitement. Despite having multiple college campuses the town is still pretty sleepy. Over the past year the town seems to have woken up and realized it was close to Boston, with local favorites Upper Crust (pizza) and J.P. Licks (ice cream) both opening stores on Central St. The town is still “damp,” though, meaning no liquor stores or bars except for on the college campuses. The commuter rail is close by, but the nearest T (subway) stop is inaccessible without a car.
Wellesley College is my alma mater, so it’s where I’ve spent most of my time. Aside from a few students looking worn-out in the local coffee shops, the college doesn’t leave much of a mark on the town. Lake Waban is beautiful, though, and plenty of town residents walk, jog, or walk their dogs on campus when the weather is nice. The college is also a great resource for families looking to hire babysitters, tutors, or general help.