Quiet local roads from Ipswich take us to Manchester by the Sea, continuing counter-clockwise for a very scenic tour of Cape Ann’s rocky coastline. All routes go through beautiful Magnolia bordering the ocean, and continue past Hammond Castle, a replication of an English medieval fortress. The short and medium routes turn back to Ipswich from Gloucester near the famous Man at the Wheel statue.The long and extra long go on to Rockport and back through Annisquam Village.

Road ride
Mitchell Lowe
Sunday, June 14, 2026 at 9am
Hammatt Street parking lot
16 Hammatt St
Ipswich MA 01938
Google map
There are no restrooms at the start.

A restroom is available across Market St at Zumi's.  Walk through the TD Bank drive thru and Zumi's is in front of you. 

 

This is is a scenic tour with frequent turns, and is not designed for pace line riding. Some roads are tight and narrow.     

Routes
Please download this latest version of the routes before each ride.
Route Miles Elev.* Print Files
Ipswich-Cape Ann - 32 Miles v2026 32 1,371 Cue sheet Send to device
Ipswich-Cape Ann - 41 mile v2026 41 1,840 Cue sheet Send to device
Ipswich-Cape Ann - 55 Miles v2026 55 2,627 Cue sheet Send to device
Ipswich-Cape Ann - 62 mile v2026 62 2,949 Cue sheet Send to device
* Elev. is the elevation gain in feet.
Route maps
32 miles, 2% unpaved
41 miles, 1% unpaved
55 miles, 1% unpaved
62 miles, 1% unpaved
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