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By Erin Price
Answer: HIKE UP

Each pair of images identifies a named intersection in Cambridge. The names fit into the grid at the bottom and the marked cells can be ordered by the area of the city where each landmark is located, spelling HIKE UP.

First image Primary street rebus Second image Cross street rebus Square namesake Area
Paperclip BENT Clock SECOND Edward F. Kelly Esq. 1
Blue ribbon FIRST Roses + levee THORNDIKE Frank L. DiLeo 1
King Charles II of England CHARLES Trivial Pursuit piece missing a wedge SIXTH Joseph L. Roberts 1
Aerial shot of MIT CAMBRIDGE Trivial Pursuit piece missing a wedge SIXTH Joseph P. Dilworth 1
Aerial shot of MIT CAMBRIDGE Chord consisting of C and E THIRD Louis J. Ferracane Sr. 1
Chord consisting of C and E THIRD Otis Redding OTIS Luigi Totino 1
Otis Redding OTIS Chord consisting of C and E THIRD Ralph W. Ferracane 1
Chord consisting of C and E THIRD William Vera King Charles II of England CHARLES 1
Broadway, Manhattan BROADWAY Child drawing a bow AMES (‘aims’) Ann Marie Sarchioni 2
Photo of Vassar campus VASSAR Seal of Massachusetts MASSACHUSETTS Mayor Brooks 2
Noah Webster WEBSTER Toasting with wine + smile PORTSMOUTH Edward Roderick 3
Rabbit outside a rabbithole WARREN Daveed Diggs JEFFERSON Jack T. Pritchard 3
Aerial shot of MIT CAMBRIDGE Rabbit outside a rabbithole WARREN James “Jimmy” Sauer 3
Tree + hobbit-hole BERKSHIRE Toilet paper + smile PLYMOUTH Joseph “Buddy” Camara 3
Aerial shot of MIT CAMBRIDGE Windsor Castle WINDSOR Joseph Versackas Sr. 3
Noah Webster WEBSTER Superman CLARK William F. Furtado Sr. 3
Open-air market MARKET Handfasting UNION Andrew J. Dobrisky 4
Column + honeybee + letter block with an A COLUMBIA County map of Massachusetts with Suffolk county highlighted SUFFOLK Charles J. Fanning 4
Cherry CHERRY Statue of John Harvard HARVARD Edith Brown Elder 4
Storm - moai + gas gauge + egg NORFOLK (NOR’EASTER - EASTER + F + YOLK) Statue of John Harvard HARVARD Frederick Kilfoyle 4
Loose plank + person absorbed in smartphone BOARDMAN Broadway, Manhattan BROADWAY James “Bumpy” Garro 4
Broadway, Manhattan BROADWAY Tree + mountain over the flag of France TREMONT John M. Gibson 4
Cross + landscape CROSSLAND Pad of paper BRISTOL Robert R. Sutherland 4
Pipes MAIN Column + honeybee + letter block with an A COLUMBIA Thomas E. Cogwell 4
Child relaxing in hammock PLEASANT The artist formerly known as Prince PRINCE Clifford A. Bonvie Sr. 5
Pearl PEARL Checklist + taser ALLSTON (ALL + STUN) Henry W. Hank Vera 5
Nurse in sanatorium FLORENCE Gary Oldman in Batman Begins GORDON Joseph C. Whitney 5
Seal of Massachusetts MASSACHUSETTS Stream + airport queue BROOKLINE Mark Sandman 5
Large collection of serial publications MAGAZINE Katy Perry PERRY Robert C. Quinton 5
Shaggy cow HIGHLAND Golf course + refusing beer GREENOUGH (GREEN + ENOUGH / NO) Charles F. Sprague 6
Child drawing a bow / gas gauge AMORY (‘aim or e’) Broadway, Manhattan BROADWAY John Philip Sousa 6
Seal of Massachusetts MASSACHUSETTS Hancock tower HANCOCK Joseph A. Brusch Jr. 6
Irving Berlin IRVING Ashton Kutcher ASHTON Olivia I. Abelson 6
Broadway, Manhattan BROADWAY Bruce Lee LEE Peter M. Moran 6
Seal of Massachusetts MASSACHUSETTS Person absorbed in smartphone with an arrow pointing at their torso INMAN Reverend Larry Love 6

The landmarks are as follows:

Landmark Group
CambridgeSide Galleria 1
Great Dome 2
Alley Cats 3
Novartis Building 4
Levitated Stone 5
Cambridge Public Library 6
Google map of all squares and landmarks

The solved criss-cross is as follows, with extraction squares highlighted in order from red to purple:

C J A M E S B U M P Y G A R R O
H A
A L
R J A C K T P R I T C H A R D
L H
E D I T H B R O W N E L D E R H E N R Y W H A N K V E R A M
S F A
J A M E S J I M M Y S A U E R J O S E P H C W H I T N E Y
F R O
A L P E T E R M M O R A N R
N J O S E P H P D I L W O R T H A B
N U C C J R
W I L L I A M F F U R T A D O S R H A O O
N S R N A N S O
G J A J D E D W A R D F K E L L Y E S Q K
F N O R L P S
E K S E E H J
R L E W M A R K S A N D M A N A E O
R R C D P J F B D H T
E A L I H D S R W N R H
V C I L B O J O H N P H I L I P S O U S A M O O
E A F E U B R S R G B M
R N F O D R A C D I E A
E E O D I G J O S E P H L R O B E R T S
N S R Y S U L J O S T E
D F R E D E R I C K K I L F O Y L E I R D O C C
L A A Y V E N Q O
A B M I R U G
R O A A I I W
R A N N M A R I E S A R C H I O N I I C N E
Y V A A K T L
L I B O L
J O S E P H V E R S A C K A S S R E N
V S W I L L I A M V E R A
E R O B E R T R S U T H E R L A N D S
O
L U I G I T O T I N O