The photo above is a view of Heartbreak Hill taken from the roof of a building onNorth Main Street in 1879. Mills line County Street on either side of the bridge which was only a few years old at that time. The mills are gone now, and Heartbreak Hill is covered with trees.
Captain John Smith sailed near Ipswich in 1608 and wrote “Here are many rising hills, and on their tops and descents are many corne fields and delightful groves.” The oldest hills in Ipswich like Town Hill are granite monoliths several million years old, but most of the hills are glacial drumlins like the Necks and Steep Hill, created by the ice age glaciers about 20,000 years ago.
Hills in Ipswich Massachusetts
Bartholomew Hill – 204′ off Linebrook behind Doyon School
Bear (Boar) Hill – off Topsfield Road near Little Turner
Bush Hill – 193′ off Topsfield Road
Castle Hill – 165′ at end of Argilla Road
Elm Hill – Marini’s Hill (Elm Hill Farm)
Heartbreak Hill – off Argilla Road 164 ft.
Jewett Hill – 212′ off High Street at Rowley line
Little Turner Hill- 197′ off Topsfield Road
Plover Hill – Great Neck
Prospect Hill – 262′ Ipswich/Rowley line
Sagamore Hill – 172′ Ipswich/Hamilton line
Scott Hill – 180′ off Topsfield Road
Steep Hill – off Argilla Road facing Crane Beach
Tilton’s Hill – near Treadwell Island
Town Hill – 184′ East of town center
Turkey Hill – 240′ between Pineswamp & Topsfield Road
Turner Hill – 250′ off Topsfield Road
Vine Hill – off Topsfield Road (Masonic Temple)
Windmill Hill – County & Essex Roads (Cable Hosp