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🏛️ CulturalWeekend · from Boston, MA

Portsmouth's Colonial Port & Isles of Shoals

Portsmouth, New Hampshire is the most intact colonial seaport in New England — Strawbery Banke, a 10-acre living history museum, preserves 40 buildings spanning 350 years of continuous occupation on the same Piscataqua River neighborhood. The Isles of Shoals, 10 miles offshore, were the site of America's most famous 19th-century murder and the painting retreat of Childe Hassam.

Day 1 — Portsmouth, NHDay 2 — Isles of Shoals & Exeter, NH
Day 1Portsmouth, NH

Day 1Portsmouth, NH

🚗 1 hr 15 min driving📍 5 stops
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Morning
🚗
Drive
Boston, MAPortsmouth, NH
1 hr 15 min8:00 AM9:15 AM
Strawbery Banke Museum
Strawbery Banke Museum
4.7
A 10-acre outdoor history museum on the original 1623 settlement site of Portsmouth, with 40 restored buildings representing every period from the colonial era to World War II. Unlike Colonial Williamsburg, Strawbery Banke preserves the physical layering of a working neighborhood — a 1940s victory garden next to a 1790s merchant's house, a 1950s diner next to a Revolutionary-era tavern. The Shapiro House, furnished to 1919, is the only museum recreation of a Russian-Jewish immigrant household in New England.
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Lunch
🍽️ Lunch10:15 AM
Black Trumpet Bistro
Black Trumpet Bistro
A Portsmouth restaurant in an 18th-century warehouse on Ceres Street above the Piscataqua River, serving Spanish and New England-influenced tapas in a room of exposed brick and low ceiling beams. The lobster flatbread, house-cured charcuterie, and the wood-fired lamb have been on the menu since 2007 for good reason; the Spanish wine list is the strongest in the Seacoast area.
4.5Bistro📍 Maps →
4 options · tap to switch
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Afternoon
Market Street Historic District
Market Street Historic District
The six-block commercial core of colonial Portsmouth survives intact from the 18th century — the Moffatt-Ladd House (1763), the Warner House (1716), and the John Paul Jones House (1758) are all open for tours and concentrated within walking distance on Market, Daniel, and Chapel streets. Portsmouth's colonial wealth is visible in the scale of the Georgian brick mansions, built when the Piscataqua mast trade supplied the British Royal Navy.
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Evening
The Wilder
The Wilder
4.3
A cocktail bar and restaurant in Portsmouth's Prescott Park neighborhood, serving New England ingredients through a serious cocktail program and a small plates menu. The bar's house shrubs and bitters are made from local herbs; the raw bar features New Hampshire's Wallis Sands oysters alongside the classic Wellfleet selection.
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Sheraton Portsmouth Harborside
A converted 19th-century brick warehouse on Portsmouth's working waterfront, with rooms facing the Piscataqua River and the working harbor. The location puts the Strawbery Banke museum and the Market Street historic district within a 5-minute walk.
Day 2Isles of Shoals & Exeter, NH

Day 2Isles of Shoals & Exeter, NH

🚗 1 hr 55 min driving📍 4 stops
🌅
Morning
🚗
Drive
Portsmouth, NHIsles of Shoals Ferry Terminal
10 min8:00 AM8:10 AM
Star Island — Isles of Shoals
Star Island — Isles of Shoals
4.5
A 95-acre island 10 miles offshore reachable by a 50-minute ferry from Portsmouth, with a Victorian-era conference center that has operated since 1897. The Shoals provided the setting for Celia Thaxter's 1873 painting retreat — Childe Hassam produced 400 paintings of the islands — and for the 1873 murders that became the subject of Anita Shreve's novel The Weight of Water. The island has no cars; the ferry schedule provides 4 hours ashore.
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Drive
Star Island — Isles of ShoalsPortsmouth Harbour — Isles of Shoals Steamship Co.
25 min9:10 AM9:35 AM
Isles of Shoals Steamship Company ferry service; check seasonal schedule and book in advance.
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Lunch
🚗
Drive
Portsmouth, NHExeter, NH
20 min9:35 AM9:55 AM
Exeter Inn & Epoch Restaurant
Exeter Inn & Epoch Restaurant
4
The Exeter Inn is a colonial revival building from 1932 on the Phillips Exeter Academy campus, with a restaurant that serves contemporary New England cuisine. Phillips Exeter — the most academically selective boarding school in the US — has occupied the town center since 1781; the academy's Louis Kahn library (1971) and the Frederick Hale gymnasium are architecturally significant.
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Afternoon
American Independence Museum
American Independence Museum
4.6
The most overlooked Revolutionary-era site in New England: the Ladd-Gilman House in Exeter was the state treasury of New Hampshire during the Revolution and housed the colony's copy of the Declaration of Independence. The museum presents two significant documents — a draft of the US Constitution and a rare broadside printing of the Declaration — in the original colonial rooms.
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Evening
🍽️ Dinner5:00 PM
Black Trumpet Bistro
Black Trumpet Bistro
A celebrated Portsmouth wine bar and restaurant in a colonial-era building on the waterfront, Black Trumpet serves locally sourced New England cuisine with global influences — seared Maine scallops, house-made charcuterie, and an exceptional craft cocktail list. One of the Seacoast's most beloved dining rooms.
4.5$$Bistro📍 Maps →
4 options · tap to switch
🚗
Drive
Exeter, NHBoston, MA
1 hr6:00 PM7:00 PM
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