Find Ben Franklin
Use a quarter-pipe on either side of the statehouse to launch up and bust through the glass into a room where Ben is, he'll run through a black door so follow him and the goal's done.
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Find The Special Guest
I guess this has to be the easiest goal in the game, as you start there's a building on your left. Go down the slope to the basement door and you'll find Jesse James.
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Combo On The RV Ramp
To do this goal you must first do the special guest goal 'Jump The Cars' to make the RV appear. Get on the RV ramp and do a combo worth 5,000 points or more. Do this when the RV is on a straight, if it's going around a corner it's easy to fall off.
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Decapitate The Statues
There are 3 of these statues, 2 of them are right next to each other outside the statehouse and the other is in the middle of the commons. The idea is you Spine-Transfer over and knock their heads off. To get both of the statehouse statues in one move use a really slow Spine-Transfer.
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Here you have to take the sick kid and his trolley up to meet Tony Hawk who is waiting at the start of the level. I recommend going through the alley between the two buildings and making a right, cut across the corner of the commons area and then head straight up the road to Tony. Swerve to avoid any surgeons... stat.
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Mark Your Territory
Spray over the 5 Spat graffiti tags. The first is outside the statehouse, the next is just down the road next to the scaffolding. Find the third up on the hospital roof, use the quarter-pipe on the ground to transfer up there. The next is in the construction area next to the huge vent quarter-pipe. The last one is outside the construction area on the wall right in the corner of the level.
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Combo The 4 Benches
This is easy, jump on the first bench and grind. You don't need to jump in between each bench, only over the bigger gap in the middle. For the other gaps just hold the grind button.
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Finest Rails In Boston
Start by grinding 'Metals' the piece of modern art in the red brick area, then head down the road and grind the railing outside the bar. Lastly grind one of the bannisters across the road by the museum.
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Great Balls Of Fire
Ollie over the flaming barrel to set your board on fire, while it's still alight do a 15,000 point combo.
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Salute The General
Spine-Transfer over the statue in the commons and pull a Benihana in mid-air.
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Skitch A Seaworthy Vehicle
There's a vehicle going around the place which looks like a boat, Skitch on it for 20 seconds. Y'arrrr!
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Slap The Signs
There are 4 'No Skateboarding' signs about the place, you have to Sticker Slap each of them. The first is at the statehouse, grind the rail, ollie and Sticker Slap it. You'll use a similar technique for the last 2 signs as well. The next sign is just down the road on the scaffolding to the left. Head further down the road and grind the blue fence to the left for the next sign. The last one is up on a wall in the red brick area, use a Wallride and grind the curved wall then ollie to the sign.
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Tag A Big Billboard
Head to the corner of the level outside the construction site. Use the quarter-pipe to launch up, get off your board and grab on to the yellow pipe. Climb up and jump to the platform, do a running jump over to the next platform and spray the billboard.
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Ye Olde Cannon Grind
Mind-numbingly simple, head over to the commons area where the cannons are and grind a cannon.
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All About The Benjamins
The idea here is to get into the bank, the doors are locked so that's out. Get speed and use the quarter-pipe outside to launch right and you'll come down through the roof.
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Combo On The High Seas
You have to score a 10,000 point combo on the boat, use a Spine-Transfer to get on there. Go back and forth the sides of the boat doing tricks until you have enough points. Use a Revert to a Manual when you land off the sides to keep the combo going.
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Skate The Liberty Trail
Firstly do a Pop Shove-It down the steps of the statehouse, ride straight down the road and air over the library mural (from the quarter-pipe on one side over to the other). Head down to the boat and Spine-Transfer aboard, climb the mast and do an Acid Drop from the top. All the relevant structures will be flashing so it shouldn't be too hard to figure out.
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Special Guest - Jesse James
Jump The Cars
Ride the road around the commons on Jesse's motorised scooter thing and jump over 3 cars to unleash the RV (used in another goal).
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Kill The Grind Blockers
Get to the air vent near the hospital and grind around the grey edge to break off the grind blockers. This has to be done on Jesse's vehicle.
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Scooter vs Wheelchair
Talk to Paulie the wheelchair guy up in the red brick area near the bank, he wants a race. Head for the commons area and make a left where the flashing quarter-pipe is, head past the library and make another left. Head towards the hospital and ride under the awning, from here head up the steps back to where the race started.
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Spine Transfer Tour
Spine-Transfer works the same way on this scooter as on a regular board. First spine over the lower end of the subway, then over one volcano shaped thing outside the hospital. Finally Spine-Transfer onto the boat.
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Next level: Barcelona >>>
Boston - Classic Mode
Collect SKATE Letters
The S is hovering over the gateway of the grand building on your left as you start. Grind the fence and ollie to reach it, then follow the road down to the red bricked area in the corner of the map. The K is on top of the wall here, get it and head towards the hospital. Use the quarter-pipe to transfer onto the first floor roof and get the A. Use the air vent as a shortcut into the dock area, the T is hovering over some wood on the far wall. Do a Spine-Transfer over the wood and use the kicker to ollie over the fence. Head left into the corner of the level and go through the archway. Air over the gap in between the quarter-pipes in here for the E.
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Collect COMBO Letters
Grind the fence for the C, use the sloped end to launch up and grind on the bus shelter for the O. Head over to the wall and air between the quarter-pipes to get the M, land in a Revert to Manual to keep the combo going. Make a left and grind down the flower beds and to the B. Manual over to the blue fence and grind it for the O. Juggling is optional (re: video :)).
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Get The Secret Tape
From the starting point go straight ahead down the road. Launch up the white part of the quarter-pipe into the cavity in the wall. Do a Caveman onto the wire and grind towards the tape, if you get low on speed use ollies.
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Backflip Down The Common Stairs
These are the steps leading down to the statue of a guy on a horse in the middle of the level. Approach the steps and use a Boneless to get extra height, do a Backflip without letting your face touch the concrete.
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Smash 5 Tea Barrels
The first tea barrel is behind you when you start, under the colorful ledge. The next is on the ship, Spine-Transfer over the fence to get on there. The next is on a scaffolding structure near the commons, either climb up or transfer up using the quarter-pipe. The next barrel is only a few feet away on the ground. The last one is up in the corner of the map in the red brick area, it's on top of the quarter-pipes.
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Grind The 5 Pigeon Rails
The first pigeon rail is in the red brick area right in the corner, use the steps to get up there and grind it. Head back towards the starting point, the next rail is a fence on the right hand side of the road. The next is the colorful ledge on the building, grind the step bannisters to launch up there. Make use of a Wallride if you don't quite make it. The fourth rail is a wire that goes above the commons area, the quickest way up is to use the little curb that goes around the commons. Timing it can be tricky, don't use much speed. The last rail is the blue fence next to the ship, grind it to the left.
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Next level: Canada >>>