Ipswich Land and Sea

Experience a unique New England Village, its pristine architecture and lovely coastline with historian-cyclist Gordon Harris.

Ipswich, Massachusetts was founded in 1634 in an area the Native Americans called “Agawam” and is known as “America’s best-preserved Puritan town.” There are more remaining first Period houses (1625 through 1725) in Ipswich MA than any other town in the country, and the historic neighborhoods of Meeting House Green, High Street, the East End, and the South Green offer well-preserved streetscapes of 17th to 19th-century residences. Resistance by the citizens and leaders of Ipswich to a tax imposed by the Crown in 1687 is commemorated in the seal of the town of Ipswich, which bears the motto, “The Birthplace of American Independence 1687.” Located on the scenic Massachusetts North Shore, away from major highways, over 50% of land in Ipswich is protected by the State, the Trustees of Reservations, Essex County Greenbelt, and the town’s Open Space program. Crane Beach is one of the most popular outdoor recreation destinations on the East Coast, with several miles of shoreline, and scenic trails winding through coastal dunes. If you love history and architecture or enjoy cycling along scenic rural roads with outstanding coastal vistas, Ipswich is the perfect day trip destination, and only an hour’s drive from Boston!

Tour Essence

  • Hear amusing legends from America’s best-preserved Puritan town by the town historian Gordon Harris
  • Ipswich Riverwalk mural offering pictorial history of the town
  • Ride the ancient roads of Ipswich with names like Great Neck, Old England, Heartbreak, Turkey Shore, Candlewood and Labor in Vain
  • Enjoy Colonial homesteads, visit a tidal stream and stand in the shadow of a towering wind turbine
  • Ride past Crane Castle, stroll along Crane Beach (and perhaps see the wreck of the Ada K. Damon)
  • Climb two glacial drumlins on Jeffreys Neck for amazing views of the Great Salt March, Plum Island, and the Atlantic Ocean
  • Taste the local produce at Russell Orchards
  • Ride through four Ipswich historic districts on the National Register of Historic Places
  • Feast your eyes on a range of architectural periods, including the Whipple House and dozens of First Period homes
  • Visit the ancient tombstones of the settlers of Ipswich in the Old North Burying Ground
  • Post-ride Visit to Ipswich Brewery


What to Expect:

Price: $125 per person or $460 for a group of four.  
Level:  Easy
Start/End Location:  Ipswich, MA
Mileage:  28 Miles
Start/End Date: Private tours available.  Contact us at 800-866-7314


Gordon Harris, an avid cyclist and Ipswich historian.

Lauren Hefferon, Director and Founder of Ciclismo Classico.


This half-day ride is led by Ipswich Town Historian Gordon Harris and begins at the Ipswich Riverwalk Mural, covering about 25 miles in one of New England’s most historic and scenic coastal communities. Starting out, our ride crosses the Ipswich River pedestrian bridge to the South Green, where the historic Whipple house is located. We wind our way along quiet back roads that were named for early Ipswich families like the Lakemans and Fellows, before stopping at Russell Orchards farm store on beautiful Argilla Rd. You’ll enjoy the gorgeous views at Crane Beach and we may even visit the wreck of the Ada K. Damon. Returning to downtown Ipswich, we’ll stop for coffee at Zumi’s or lunch at one of the town’s many casual eateries. We continue through the Meetinghouse Green and East End historic districts, where Gordon will share a few legends and a bit of history from “America’s best-preserved Puritan Town.” Next comes a seven mile loop to Great Neck with the Great Salt Marsh on either side, and climb the glacial drumlin with scenic vistas of Plum Island, Cape Ann and the Atlantic Ocean. Turning back to town, the ride follows historic High Street, home to over two dozen First Period houses constructed before 1720 to the Old North Burying Ground. You can view fascinating inscriptions on 17th and 18th Century tombstones before we head back to our start location and finish the ride.


Questions? Call Ciclismo Classico at 800-866-7314 today!


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