Top 9 cultural & heritage things to do in Portsmouth

1. Portsmouth scavenger hunt walking adventure

Two hours of exploration, solving riddles at historical sites and parks, plus capturing memories along the way.

2. Private bike tour of Portsmouth

Three-hour guided bike tour through Portsmouth’s historic streets, coastal views, and hidden spots; includes bike fitting and safety briefing 30 minutes before start.

“During our brief first visit, we aimed to explore as much as possible. We reached out to Dawn to arrange a quick-paced private tour, mixing neighborhood highlights and island locations. She paired us with Steve, who was ideal for our needs—keeping stops and historical details brief as we requested. His deep knowledge of the area made our trip engaging and efficient, allowing us to cover everything we wanted. I highly advise this early in your stay. Great job, team!”— kathyriz673

3. E-bike scenic tour of Portsmouth's beaches and harbors

Three and a half to four hours on a pedal-assist bike along 17+ miles of coastline, historic sites, coastal mansions, and local stories.

“I had a fantastic experience on this tour with Don. It was a great way to explore Portsmouth in the morning. We cycled through Prescott Park, Pierce Island, and all the way to Newcastle Island. Don's storytelling and historical insights were truly enjoyable. I learned quite a bit about Portsmouth's history and some interesting tidbits. This is an excellent method to experience Portsmouth, and I highly endorse it.”— annai938

4. Interactive scavenger hunt in Portsmouth

Two to three hours, self-guided with a remote host — explore Portsmouth's history and culture through creative clues and challenges.

“It was a really enjoyable experience! It would have been even better with a larger group, but now I know for next time.”— Discover62598289195

5. Islands and Harbor bike tour in Portsmouth

Approximately two hours, 8-10 miles by bike — scenic sights, stories of maritime history, and coastal views around Portsmouth and New Castle Island.

“The tour guide demonstrated great knowledge and was attentive to safety when I struggled with the 7-speed bicycle, given my lack of experience. They adjusted the route while maintaining our engagement for the entire duration.”— Gwenda B

6. Wine and gourmet tasting at Rockingham in Portsmouth

Ninety-minute guided tasting at Rockingham, featuring curated wines and gourmet bites paired with local history.

“Paul from Flaghill Winery delivered an engaging talk about his wines, detailing why each was paired with specific hors d'oeuvres during our tastings. I found it fascinating to learn how the climate contributes to unique varietal grapes and their role in creating distinctive wines. The chef's exceptional selections perfectly complemented the wines. It was a truly delightful experience.”— Sightsee670510

7. Portsmouth bike tour of historic landmarks

Two hours on a bike, covering 6-8 miles, visiting key historic sites and neighborhoods in Portsmouth with an informative guide.

“Donna was amazing! The tour was incredibly informative, and Portsmouth is a beautiful city. Cycling from one historic site to another and along the waterfront added to the enjoyment. It surpassed all expectations! I highly recommend Donna and Port City Bike Tours.”— E5909PEsallyr

8. E-Bike and bike rental for 3 hours in Portsmouth

Three hours of independent exploration on a 7-speed bicycle or e-bike, with included helmet and route guidance.

“I am extremely disappointed with this company. We had booked a cultural/history tour more than three months in advance and communicated our flight concerns multiple times. However, they canceled the tour at 5:00 pm the night before, sending a very impersonal email. This was meant to be our first activity in New Hampshire for our anniversary weekend, leaving us no time to find another option. Our evening plans prevented us from searching, and we lost half of our vacation just waiting. This situation is incredibly frustrating. I understand cancellations can happen for various reasons, but they canceled simply due to low attendance, prioritizing profits over customer experience. In my years of traveling, I have never encountered a tour cancellation for that reason. It’s unreasonable to provide such short notice, especially for travelers investing their time and money. They should have notified us days ahead so we could arrange another activity. Their customer service was lacking, reflecting poor business practices. They tout “legendary customer service” on their website, but they've proven otherwise. This is, by far, the worst customer service I've experienced regarding a vacation tour, and I cannot recommend them.”— winchela

9. Self-guided haunted walking tour of Portsmouth

Explore Portsmouth's haunted sites at your own pace using a GPS audio app and EMF reader, featuring infamous locations and spooky stories.

“This tour offered a unique self-guided experience in the city. We could explore at our own pace, taking breaks to shop and eat before continuing. The information about each site was engaging.”— Cheryl C