Bay View
Downtown
Downtown: Boulevard/The Cut
East Gloucester: East Main Street
East Gloucester: Eastern Point
100

This Civil War General built a summer home here in 1866

Benjamin F. Butler

100

Name as many restaurants you can that once occupied diner cars at Main and Chestnut

Kings, Supreme, Chicks, Michele’s Cape Ann Diner, Hesperus Diner

100

The classic TV show filmed an iconic scene here in the 1970s

Bewitched

100

The Lobster was once the site of this old local favorite for seafood.

Bob’s Clam Shack

(Smokin Jim’s BBQ for partial credit)

100

 The name of A. Piatt Andrew’s House on Eastern Point

Red Roof

200

Give a local name for the leaning old cottage overlooking the Bay

The “Tiltin’ Hilton” (known by locals today)

Wuthering Heights (according to GDT article)

200

The location on Main Street where Gloucester kids of the 1970s and 1980s got their first bicycle

Giles of Gloucester

200

Local legends say this famous Gloucester captain posed for the Man at the Wheel sculpture

Clayton Morrissey

200

The Gloucester Writer’s Center is located in this poet’s former home.

Vincent Ferrini

200

The family that owned Eastern Point when it was farmland

The Niles

300

The family that ran the Bay View variety store along Washington Street

The Vicari's

300

Name one of downtown’s two movie theaters

North Shore

The Strand

300

The name of the sculptor who designed the Man at the Wheel

Leonard Craske

300

Before it was known as Beacon Marine, it was:

Robinson’s Marine

Reed & Gamage/Gorton’s property

300

The name of the hotel built in the former Civil War-era fort

The Ramparts

400

The local restaurant credited with popularizing fried calamari

The Gloucester House

400

Long time residents will remember this restaurant before it was Poseidon’s

Boulevard Sweet Shop
400

The type of fishing that “Michigan Bears” brought to Gloucester

Gillnetting

500

The downtown bar at the center of Gloucester election nights

Kelleher’s