The Portsmouth Harbour Trail is similar to Boston's Freedom Trail in that it links together many of the historic homes, the working waterfront, colorful Prescott Park, vibrant Market Square - and of course you also pass by the boutique shops, restaurants, art galleries, etc. of downtown Portsmouth. The guided walking tour takes about an hour, and is a great introduction to the 400-year history and culture of Portsmouth. Even if you're not a huge history buff, the tour guides keep it interesting and fun. And though they may tell you about the shady history of Prescott Park (yes, there used to be brothels in Portsmouth) the comments and jokes are family-appropriate.
Tours run Memorial Day to mid-October. You can buy tickets at the Greater Portsmouth Chamber of Commerce, 500 Market St., or right at the Market Square info kiosk where the tours start. Tours are weather-dependent, so call the Portsmouth Chamber at 603-610-5510 if you have questions. Off-season you can also pick up a self-guided tour book, so you can still enjoy the Trail.
The tour begins and ends in Market Square, the heart of downtown Portsmouth. You're right in front of Breaking New Grounds so grab a coffee and sit at one of the outdoor tables ...or head over to Popover's for great salads, quiches, pizzettas, and amazing selection of baked goodies. There is no shortage of fantastic restaurants in Portsmouth, so stay awhile and enjoy!