Portsmouth & New Castle: Islands Bike Tour with Harbor Stories

Summary

Cycle Portsmouth’s islands, bridges and coastal history with a local guide

You’ll pedal along Portsmouth’s riverside paths and over bridges to New Castle Island, guided by a local who brings harbor stories to life. Expect stops for lighthouse views, time at Great Island Common’s oceanfront, and glimpses of working docks—all with bikes and helmets included. You’ll leave feeling like you’ve seen more than just postcard scenes.

What’s the experience like?

First thing I noticed was the river — that briny smell, kind of sharp but clean. We’d barely started pedaling in Portsmouth before our guide, Tom (he grew up here), pointed out a lobster boat bobbing near Peirce Island. The morning felt cool on my arms. I kept glancing at the water, half-distracted by gulls squabbling over something shiny. Tom told us about the Prescott Sisters and how they used to walk this same route, which made me slow down a bit just picturing it.

We crossed one of those old steel bridges—honestly, I was nervous at first because you can feel it rumble under your tires. But then you’re looking out at the Atlantic and suddenly there’s New Castle Island ahead, all these weathered houses and people waving from their porches like they know you. There was this moment when we stopped by the docks and I caught the smell of fried clams drifting from somewhere (wish I’d asked where). Tom joked about “Live Free or Die” being more than just a motto around here—he said it with this crooked grin that made me laugh.

I didn’t expect to care much about lighthouses but seeing three in one ride felt oddly grounding. At Great Island Common we parked our bikes for a minute; someone’s dog ran past us straight into the waves. The air tasted salty and my legs were jelly but in a good way. Fort Stark looked almost forgotten, grass pushing through old stone—I touched the wall just to feel how cold it was. People talk about “must-see sites” but honestly, it’s these small pauses that stick with me most.

Step-by-step itinerary

Day 1 — Coastal ride with historic storytelling

• Hear story about Prescott Sisters
• Pass through Peirce Island
• Stop to discuss Historic Hotel
• Stop to discuss Portsmouth Naval Shipyard
• Stop to talk about 7 forts and Isle of Shoals
• Discuss Captain John Stark and first settlement

Top questions

How long is the Portsmouth & New Castle bike tour?

The tour covers about 8-12 miles along the coastline, islands, and harbor areas.

Are bikes and helmets included in this tour?

Yes, both bicycles and helmets are provided for all participants.

Is this bike tour suitable for beginners?

Yes, it’s suitable for all physical fitness levels; specialized infant seats are also available.

What sites do we visit during the tour?

You’ll see Peirce Island, New Castle Island, three lighthouses, Great Island Common oceanfront, Fort Stark ruins, and Portsmouth Market Square.

Does the tour include stories or history?

Your local guide shares stories about maritime history, local legends like Captain John Stark, and details about historic sites along the route.

Can children join this bike tour?

Infants and small children can ride in a pram or stroller; specialized infant seats are available.

Where does the tour start?

The ride begins in Portsmouth and explores both Portsmouth and New Castle Island areas.

What’s included

Your day includes use of a bicycle and helmet for each rider plus an expert local guide leading you through Portsmouth’s riverside paths, over bridges to New Castle Island with stops for stories at historic spots—so you can just show up ready to ride without worrying about gear or navigation.