Checkpoint 4..."I Know Nut-ting!"
The establishment that serves as Checkpoint 4, near Harvard, shares its name, but not its spelling, with the last name of the actor who portrayed the able Sergeant Kinchloe in this TV comedy.     Answer

 

Checkpoint 5...Do They Write Many Tickets?
Standing south of the Charles River, find and photograph the posted speed limit for river traffic east of the Weeks Bridge. Make sure you and your teammate are in the photograph. Start running again...     Answer

 

Checkpoint 6...Don't Feed These Birds
In Charlestown, artsy ravens and belted kingfishers, among others, observe the memory of past sacrifices. Take a photo with our feathered friends because they are checkpoint 6.     Answer

 

Checkpoint 7...Will You Cut To The Chase?
Find the play in which a character muses as set forth below and you will know the name of the North End establishment that serves as Checkpoint 7

True, I talk of dreams/Which are the children of an idle brain/Begot of nothing but vain fantasy/Which is as thin of substance as the air/And more inconstant than the wind.     Answer

 

Checkpoint 8...I'll Bet Dentists Love This Dish!
Checkpoint 8 is a copper lobster near Rowe's wharf. Picture time.     Answer

 

Checkpoint 9...Cocktails!
Checkpoint 9 was established in 1826, serves beer, and is located near the Freedom Trail. Any signage will do.     Answer

 

Checkpoint 10...Semper Fi!
This Charlestown native and Boston Latin graduate gave his life for his country. Find his place of honor in the Public Garden and get your photo there cuz it is Checkpoint 10.     Answer

 

Checkpoint 11...Boston Math in the Red Light District
Checkpoint 11 is a red box with a red light on top, not to far from Louisburg Square (why is there a fence around that place anyway?) Checkpoint 11 bears the number represented by the following equation...(A times B) plus C.

A: (Tom Heinshon * DJ) - Bill Russell + Walter Brown
B: (Bob Cousy * DJ) - JoJo + (Satch/(Bird -KC Jones))
C: Red Auerbach
Take a picture with the box and make sure we can see the number.     Answer

 

Checkpoint 12...I Don't Think These Will Float
Find at least 20 stone sailboats and take a photo with at least one of them cuz they are Checkpoint 12.     Answer

 

Checkpoint 1...Checkmate!
Find the circular bronze plaque flanked by 30 green benches near water. Ignoring the eastern benches completely, imagine that the western benches are equal squares on a chessboard. Assume the southwestern most bench is the lower left hand corn of the chessboard you are playing on. Take a photo standing on the bench corresponding to the location of what would be the Queen's Pawn at the start of a standard chess match. That bench is Checkpoint 1.     Answer

 

Checkpoint 2...Who's Your Pal?
Checkpoint 2 is apparently a likeness of an Argentinean President who was a buddy to the Americans. It says so right there on the statue in the Backbay area. Get your photo with our buddy cuz its Checkpoint 2.     Answer

 

Checkpoint 3...How You Doin?
Checkpoint 3 shares its name with the last two words of the title of this absurd film by a famous filmmaker who plays a clarinet. Any signage will serve as Checkpoint 3.     Answer