Portsmouth

Portsmouth, NH packs more personality per square block than most cities ten times its size. About 22,000 people live here, but on a summer Saturday it can feel like the whole Northeast showed up for lunch. The colonial-era downtown along Market Square has brick buildings dating to the 1700s sitting cheek-by-jowl with James Beard-nominated restaurants. The Piscataqua River separates New Hampshire from Maine right at the city's edge, and the Naval Shipyard (technically on Seavey's Island in Kittery, Maine) has been a working presence since the 1800s. The Treaty of Portsmouth ending the Russo-Japanese War was signed here in 1905. New Hampshire has no income tax and no sales tax, which matters when you're buying that $18 craft cocktail downtown and at least know the price on the tag is the actual price. Remote workers flooded in after 2020, drawn by the walkable downtown and coastal access, and that has pushed housing costs up significantly. The dining scene genuinely punches above its weight for a city this size.

Portsmouth is one of the safer small cities in New England. The violent crime rate sits at 0.14% and property crime at 1.04% — both low. Downtown at night is active and well-lit, particularly around Market Square, Bow Street, and the waterfront. The city is small enough that it doesn't have genuinely rough neighborhoods in the way larger cities do. Standard precautions apply: don't leave valuables in your car (break-ins do happen in parking garages), and keep an eye on your bag during crowded summer events like Market Square Day and the Chowder Festival when the streets are packed with 50,000 people. The waterfront areas around Prescott Park and Peirce Island are safe for evening walks.

Downtown Portsmouth is genuinely walkable once you're parked. The problem is getting parked. Foundry Place Garage on Foundry Street runs $1/hour with a $20 daily cap — the better deal compared to Hanover Garage's $2/hour. Free parking exists at Peirce Island (115 spaces) and the South Mill Pond area lots, but those fill by 10am on summer weekends. The ParkMobile app works for meters. Enforcement runs 9am–8pm Monday–Saturday. C&J Bus Lines runs hourly service between Boston's South Station and the Portsmouth Transportation Center, which is a useful option if you're coming from the Boston area. COAST bus handles local Seacoast routes. But here's the thing: you really do need a car for anything beyond the downtown core. The walk score of 47 tells the story — downtown is fine on foot, but Elwyn Park, the beaches at Rye, or a trip up the coast requires wheels. Portsmouth International Airport at Pease (PSM) is about 5 miles from downtown, with Enterprise Rent-A-Car on-site.