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City Square
City Sq & Main St, Charlestown, MA 02129
Known as "the Gateway to Boston," City Square marks the spot where Charlestown was original settled in theMore 17th Century. The park provides a surprising oasis at a major intersection and offers excellent views of downtown Boston. It features 70 different varieties of trees and perennials, as well as a fountain and monuments to Charlestown veterans and its historic role in the U.S. Navy. The park hosts dozens of civic events and may be used for private functions as well. It is maintained, in part, by the nonprofit organization Friends of City Square Park.
Thompson Square
Main St & Austin St, Charlestown, MA 02129
Thompson Square provides residents and visitors a place to catch their breath in the middle of a hectic intersectionMore along Main Street. It's a small park that pays homage to what once was a bustling corner of commerce for historic Charlestown, but is now a spot where dog owners can take a break with their pets or for neighbors to stop and say hello to each other. From the park, you can get a good look of One Thompson Square, a Victorian Gothic structure built in 1875 just after Charlestown ceased to be an independent city and became part of Boston.
Max and Dylan's City Square
1 Chelsea St, Charlestown, MA 02129
Max and Dylan's is a warm and hip restaurant and bar, with an inclusive attitude. Located on the Freedom Trail, rightMore next to the North Washington Street bridge, it is convenient for everyone from the after-work crowd to people looking for food and fun before a Garden event, to families with children. There is a kids' menu offering $4.99 meals, which include WikiStix and a full pack of Starburst. The managers make a point to check in with every guest during their visit, as having happy, repeat patrons is their number one priority.  The spacious main dining room has 25 tables (no booths) and there are 14 tables in the bar area. The walls are covered with beautiful, large prints of Boston, photographed by a member of their own staff. On-street parking is available, as well as the $7.00 "in by 5pm, out by 7am" Constitution Marina parking lot a few doors down. Brunch is offered on Sundays from 10am until 2pm.