The Hill - Highlights of the Hidden Neighborhoods of Portsmouth City View Bike Tour:

Former North End / Italian “Little Italy”
The Hill
South End and Prescott Park
Strawbery Banke
Wentworth Coolidge Mansion
Frank Jones Brewery - West End
Creek Neighborhood - Christian Shore

• Portsmouth - The destruction and preservation of Little Italy. Over a dozen colorful wooden houses are squeezed up against the towering Marriott and Hilton Hotels. In the early 1970s, the concept was that dilapidated buildings bred ragged people. After World War II, most cities demolished thousands of “blighted” urban areas across the nation, replacing them with high-rise apartments, shopping malls, and hotels. In Portsmouth, much of historic Vaughan Street was lost and replaced with a parking garage and open lots. The tour passes a collection of preserved historic homes saved by urban renewal before moving into this area for preservation.

• Strawbery Banke Museum - Strawbery Banke Museum began as a “save our history” effort by the citizens of Portsmouth. In the late 1950s, Puddle Dock, an area of dilapidated homes near the Piscataqua River, was targeted for urban renewal. All the “substandard” homes in Puddle Dock — some of which dated back to the 1600s — were to be torn down and replaced with modern buildings. That was until city librarian Dorothy Vaughn addressed the Portsmouth Rotary Club one day in 1957.

That day Vaughn “laid it on the line” for the Rotary Club, telling them that every time one of the old houses was torn down or an antique piece of Portsmouth furniture was shipped out of town, the city was losing its past. The Rotary Club was galvanized into action, and while Puddle Dock did undergo urban renewal, much of it has been saved as a historic museum.

• Wentworth-Coolidge Mansion - Explore the beautiful Little Harbor.

• Wentworth-Gardner House - The Wentworth Lear Historic Houses are a pair of adjacent historic houses on the south waterfront in Portsmouth, New Hampshire. Both buildings and an 18th-century warehouse were owned by the Wentworth Lear Historic Houses and operated as a house museum. Only the Wentworth-Gardner house is a museum.

• Prescott Park - Prescott Park is a ten-plus acre waterfront park in Portsmouth, New Hampshire, United States. The land was purchased in the 1930s by two sisters, Josie and Sarah Prescott. The sisters, public school teachers, had used an inheritance to systematically purchase and clear properties along the Piscataqua River.

• Strawbery Banke Museum - Strawbery Banke is an outdoor history museum located in the South End historic district of Portsmouth, New Hampshire. It is the oldest neighborhood in New Hampshire to be settled by Europeans, and the earliest neighborhood remaining in the present-day city of Portsmouth.

• Major General Fitz John Porter Statue - Porter was a prominent Union Brevet Major General during the American Civil War, celebrated for his role in the Peninsula Campaign but infamously court-martialed and cashiered for his actions at the Second Battle of Bull Run in 1862. A highly regarded officer in the pre-war army, he was eventually exonerated and reinstated to the army in 1886 after a long campaign to clear his name.

During the Second Battle of Manassas (Second Bull Run) in August 1862, Porter’s V Corps was transferred to Maj. Gen. John Pope’s Army of Virginia. Porter, who held a low opinion of Pope, was accused of disobeying orders to attack on August 29, 1862, arguing that the attack would have been futile against strong Confederate positions. Following the Union defeat, a court-martial found Porter guilty of disobedience and misconduct, resulting in his dismissal from the Army on January 21, 1863.

• Helmet included
• Bicycle usage provided

• Tips and gratuity

This bike tour seamlessly blends history, art, culture, and local Portsmouth stories, making it a perfect choice for anyone who loves heritage and preservation. Riders travel with a guide along quiet streets, peaceful roads, and tucked-away neighborhoods, stopping at historic landmarks and sites along the way.

The guide shares fascinating tales of maritime history, fishing, and the historic preservation efforts that led to the creation of house museums and Strawbery Banke—a collection of preserved 18th- to 20th-century homes saved during Urban Renewal.

• Pedal to the North End and hear the stories that bring this former neighborhood to life
• Visit The Hill, where 19th-century homes were saved and relocated during Urban Renewal
• Explore the riverfront of Prescott Park, a former neighborhood of bars and brothels
• Pedal to Little Harbor and hear stories about the royalty at the Wentworth-Coolidge Mansion
• Visit the runaway Ona Judge mural. Save on our site

For a full refund, cancel at least 24 hours before the scheduled departure time.