Historic Neighborhoods of Portsmouth Bike Tour

Delve into the heritage of Portsmouth’s historic neighborhoods

Portsmouth’s historic neighborhoods are a treasure trove of fascinating cultural regions, buildings, parks, and sculptures, each telling their own extra-special segment of Portsmouth’s rich and complex story.

This enjoyable and educational bike tour brings you on a fun journey of discovery through the fascinating neighborhoods of Portsmouth, from ‘Little Italy’ to Bohenko Park, accompanied by an expert guide ready to bring Portsmouth to life before your eyes.

Your brilliant bicycle tour begins in Portsmouth’s North End, nicknamed ‘Little Italy’. Your guide will divulge how this area has developed significantly since the 1970s, bringing you and your bike to The Hill for a closer look at the preserved historic buildings that stand as testament to Little Italy’s enduring character.

Having explored The Hill, you’ll cycle to Little Harbor for a gorgeous view of the secret cove and back channel with the opportunity to hop off your bike and follow your guide on a sweet little walk to the river. In these idyllic surroundings, your guide will tell insightful stories of the Wentworth Coolidge Mansion and George Washington’s visit to the area all those centuries ago. This is also the perfect place for a photograph of Portsmouth!

Pedal onwards to the gorgeous Prescott Park to learn a little more about the development of Portsmouth over the last few decades before following your guide to the former Frank Jones Brewery Lane. The ‘King of Ale’ held quite a reputation in these parts back in the day - let your guide tell you the intriguing story!

Finally, bike into Bohenko Park for a memorable visit to the Endeavor statue - a fabulous finale to your fascinating bicycle tour.