Wisebread is running a contest of cheap things to do in your city here.  Apparently you blog about cheap fun things for under $5.  As a student I used to thrive on freebies.  Here we go.

First, walk the Freedom Trail in Boston.  Sure there are guided tours for $14, but this way you can go at your own pace.  It’s got 14 stops and is 2.5 miles so perhaps pacing your tour is better.  Plus you can download your own free tour onto your mp3 player from Boston.com or pay the Freedom Trail for their Steven Tyler (Aerosmith) version.  It’s a fun hike and it ends up at the U.S.S Constitution, where you can take a free tour of Old Ironsides!  The oldest commissioned warship.

Also the Freedom Trail starts in Boston Common, a free, open area park.  It used to be used for hangings, but now you can see the state capitol with the golden dome and people watch tour groups passing by. 

Also in the Boston Public Gardens across the street from Boston Common you can take your children to a Swan Boat Ride.  These boats are in the shapes of Swans and the conductor propells you around a little pond by paddling by biking.  Each ride is $2.50/adult and $1.00/child.  Many children seem to enjoy it.

Second, ride the Minutemen Bike Trailway.  It passes through historic areas where the American Revolution began.  It runs through the communities of Cambridge, Bedford, Lexington, and Arlington for a combined route of 11 miles.  You are also allowed to walk/run/rollerblade but 11 miles is somewhat far.  I have to say it’s a fantastic morning bike ride.  Many people use it to commute into the city as well.

Third, check out Quincy Marketplace and Faneuil Hall.  With a ton of shops, you can spend a leisurely afternoon window shopping and perhaps grabbing a snack for $5 within the Colonnade.  It’s very lively and there are tons of spots to sit and enjoy people watching and street performers.  Across the street you can see the Boston Aquarium and the Harbour.  A stroll along the harbour can be fun and entertaining. 

Fourth, stroll down Newbury Street and window shop. Though way above the $5 limit, the street is filled with fantastic people watching restaurants and shops.  You can sometimes see movie stars chilling out.  Also stop by JP Licks and get a cone for $3 and continue walking to Copley Square.  There are a ton of shops in the area, the Trinity Church, and the Public Library.  The Library has a map exhibit to enjoy and the is just lovely to walk around and sit in the courtyard with a book.

Next, enjoy the a few hours touring Havard University and the surrounding square.  It has old world charm with the cobblestone streets and shops.  Tours are free and interesting.  After leaving Harvard walk down to the Charles River.  On both sides there are areas of where pedestrians are able to bike, walk, and rollerblade freely called Memorial Drive and Storrow Drive.  About 3 miles in length you can enjoy the breeze of the river and watch people compete for rowing races.

Finally, I have to list the open museum hours in Boston.  The Museum of Fine Arts on Wednesdays is free between 4-10pm.  The Children’s Museum is $1 on Fridays from 5-9pm.  Boston’s Zoos are half off making them $6 on the first Saturday of the month, a bit over but still not a bad deal.  Harvard Art Museum is free if you go on Saturdays before noon. And the Havard Museum of Natural History is free on Sunday mornings or Wednesday afternoons from 3-5pm for Massachusetts Residents.

There’s still more free fun stuff to do in the surrounding area as well.  Hiking the Berkshire Mountains, checking out Cape Cod for cranberry picking, etc.  I bet your cities are just as fun, it just takes a bit of creativity to get out there and do it.  Hope everyone enjoys this list.  I’ve done all of these freebies and more.