The clues are in alphabetical order, and solve to:
- AMERICA'S CUP
- BARRE
- BIRTHRIGHT
- BULL
- BUSH
- CHART
- CLAY
- COMING
- CRAVEN
- CROAK
- CURRY
- CURTAIN
- DANK
- DAUPHIN
- DEAL
- DOLLAR
- DRAKE
- DRESSER
- DRILL
- DWARF
- ELVEN
- EXCELSIOR
- EXTENSION
- FLINT
- FRUIT
- FURNACE
- FURROW
- FUTURITY
- GOLD
- HENCHMAN
- HOMEFIELD
- HUGER
- LARGE
- LIGHT
- MAIDEN
- MASON
- METHYL
- MOODY
- MYOPIA
- NICE
- NURSERY
- OKIE
- OLIGOCENE
- ORTHODOX
- PEERLESS
- PLANTERS
- POTTER
- PROCTOR
- RAINBOW
- RANSOM
- ROPES
- SAILMAKER
- SALUTATION
- SHADOW
- STAPLE
- TASKER
- TERAGRAM
- TERRA FIRMA
- TRAVERSE
- VETO
- WELD
- WHEATSHEAF
- WINGTIP
- WITCH
As the flavortext suggests, these 64 answers with brackets are associated with some of the biggest cities in colonial America. Specifically, the eight largest: Philadelphia, New York City, Boston, Baltimore, Salem, Newport, Providence, and Charleston. These are depicted, in outline form, in the image above the clues.
Each of these answers corresponds to a street in one of those cities. Each city is assigned a letter; Charleston is A, for instance. In the brackets are the first letters at each of the streets' ends. (Where streets end in a dead-end, a bullet is present; where the terminal streets start with the same letter, the first two letters are provided.)
- Charleston (A): SAILMAKER / BARRE / DRAKE / BULL / MAIDEN / HUGER / BIRTHRIGHT / COMING
- Baltimore (B): LIGHT / CHART / TERRA FIRMA / SHADOW / FURROW / GOLD / CURTAIN / PEERLESS
- Philadelphia (C): LARGE / WINGTIP / ORTHODOX / TASKER / DEAL / DAUPHIN / NICE / WHEATSHEAF
- New York City (D): EXCELSIOR / MOODY / CRAVEN / DWARF / STAPLE / FUTURITY / DANK / CROAK
- Newport (E): AMERICA'S CUP / DRESSER / WELD / CLAY / CURRY / BUSH / POTTER / EXTENSION
- Providence (F): OKIE / DOLLAR / TRAVERSE / METHYL / VETO / HOMEFIELD / DRILL / FURNACE
- Boston (G): ELVEN / RANSOM / OLIGOCENE / SALUTATION / TERAGRAM / MYOPIA / FRUIT / HENCHMAN
- Salem (H): MASON / FLINT / PLANTERS / WITCH / PROCTOR / NURSERY / ROPES / RAINBOW
The ordering is given by the subscripts. "Following" the streets in order by connecting the "end" of a street to the "beginning" of the next forms a letter in each city. From south to north (and roughly west to east, as well as in the order of the letters), those letters spell TRAIPSES.
