Base: a downtown hotel or inn near Market Square, both nights. Take an early C&J bus from Boston South Station or Logan Airport to the Portsmouth Transportation Center, about 1½ hours, then a taxi into town, about 10 minutes. Market Square, Ceres Street and the Harbor Trail are free to walk. Pace: easy: a morning bus, then about two miles of flat downtown walking with long sit-down meals in between.
The bus up and breakfast on Penhallow Street
Book seats on an early C&J bus from South Station. It is a comfortable ride up Interstate 95, past the marshes of the North Shore and across the Merrimack, and you can drop bags at the hotel before the day starts.
Where to eat: walk to Ceres Bakery on Penhallow Street, a small bakery a block from Market Square, for coffee, soup or a slice of something baked that morning. Sit at the long table if it is free; it suits a group.
Check the bus timetable on the C&J site the week you go. Weekend and holiday schedules differ, and booking ahead keeps the group together on one bus.
Market Square and the North Church
Walk out into Market Square, the center of Portsmouth since the 1700s, where Congress Street, Pleasant Street and Market Street meet under the tall white steeple of the North Church. The brick commercial blocks around it hold cafés, bookshops and small stores, and in winter the square is often hung with lights.
Wander Market Street down toward the river, and look up: many of the upper floors still have their old brick fronts and arched windows.
Expert tip: pick up the Portsmouth Historical Society’s Harbor Trail map before lunch. The marked walking loop links Market Square, the waterfront and the old South End, and it gives the afternoon a route without anyone having to plan it.
Lunch at Row 34 and the Ceres Street tugboats
Where to eat: lunch at Row 34 Portsmouth, an oyster bar and restaurant a few minutes’ walk from Market Square. Order a few dozen oysters and some plates to share; it is a good table for a group.
After lunch, walk down to Ceres Street on the river. The red-and-black tugboats that work the harbor are often moored along the wharf here, beside brick warehouses that once stored ships’ goods. Watch the current run fast on the Piscataqua; it is one of the swiftest-flowing rivers on the East Coast.
Then follow the Harbor Trail along Bow Street and back up through the old streets toward the hotel to rest before the evening.
Ice cream and dinner at Moxy
On the walk back, stop at Annabelle’s Natural Ice Cream on Ceres Street for a scoop, even in winter; it is a short step off the waterfront.
Where to eat: dinner at Moxy, a small-plates restaurant in the middle of downtown with a menu built on New England ingredients. Order several plates for the table and share them around.
After dinner, the downtown bars and the evening lights on Market Square are all a few minutes’ walk from the hotel.
Where to eat and stop
- Breakfast · Ceres Bakery — Coffee, soup and baked goods at the long table. Why here: On Penhallow Street, a block from Market Square, an easy first breakfast for the group. Well reviewed for fresh pastries and breads.
- Lunch · Row 34 Portsmouth — Oysters and shared plates for the group. Why here: Downtown, with oysters and beer that suit a group of friends sharing plates. Well reviewed by visitors.
- Dinner · Moxy — Small plates of New England food to share. Why here: Downtown, small plates made for sharing round the table with friends. Well reviewed by visitors.
- Quick stop (snack): Annabelle’s Natural Ice Cream — A scoop on the walk back from the river. Why here: On Ceres Street by the harbour, a sweet stop on the evening waterfront walk. Consistently strong reviews from visitors.
Boston South Station → the Portsmouth Transportation Center by C&J bus: about 1½ hours. The transportation center → downtown: about 10 minutes by taxi. Ceres Bakery → Market Square: about 2 minutes on foot. Market Square → Row 34: about 10 minutes on foot. Row 34 → Ceres Street: about 10 minutes on foot.
Where to stay
- A hotel near Market Square — a hotel within a few blocks of Market Square; check-in after 3 p.m., bags held earlier.
- An inn in the South End — or an inn in the quieter streets of the South End, near Strawbery Banke.
Dinner: at Moxy downtown; book a table for the group.
Tomorrow: Strawbery Banke, about 5 minutes on foot from Market Square.
Bad-weather plan
Cold rain on Day 1? Keep lunch long at Row 34, spend the afternoon in the bookshops and cafés around Market Square, and skip the Harbor Trail until Day 2.
Stay: downtown base · Anchor: the Ceres Street tugboats · book the bus both ways
Good to know: Downtown Portsmouth is small: Market Square, Ceres Street, Strawbery Banke and Prescott Park are all within about a 10-minute walk.
