COVID-19 update: When planning your trip, check with museums and other attractions or diversions about their current pandemic-related policies, as well as Maine's COVID-19 website. Maine lifted its quarantine and COVID-19 requirements for out-of-state visitors on May 1 but may reinstate them for arrivals from particular states if their caseloads spike.
The minute you round the corner into Castine, you know you've arrived somewhere special. This coastal Maine town seduces visitors with its handsome Federal and Georgian homes, elm-lined streets, colorful gardens, college campus and serene views of windjammers and working boats cruising Penobscot Bay — but it's more than a pretty face. Long visited by Native Americans and occupied continuously since the early 1600s, Castine played a significant role in America's early history. Here, prowl through forts, poke around museums and read interpretive signage commemorating historic battles, burial grounds, trading posts and other historical sites and events.
Most first-time visitors to this bordering-on-precious village (population: less than 1,000) wonder why such a fine collection of historical sites dating from pre-Revolutionary America through the Civil War exists in this off-the-beaten-track spot. “It's amazing how many small fortifications, batteries and redoubts are scattered around town,” says Lisa Simpson Lutts, director of the Castine Historical Society.
The reason? “Location, location, location!"
Located about 137 miles northeast of Portland, Castine juts into the northern end of Penobscot Bay, tipping a peninsula framed by the Bagaduce and Penobscot rivers. Early explorers knew controlling the coast and rivers meant controlling the interior lands, the source of animal furs and timber that could be sent to Europe and traded for supplies.
"Back then, people got around by waterways. There were no roads. You needed to have a deep harbor, and this town has an incredibly deep and protected harbor,” Lutts says. It also has height, she adds, referring to the gentle rise from waterfront to an elevation approaching 200 feet. That's why the French, British, Dutch and Americans fought for governance from the early 17th century, when it was part of Massachusetts, until the early 19th century, with control ping-ponging among them.
These days, Castine is not only a living memorial to past turmoil but also a snapshot in time. By the mid-1800s, the town was a major commercial port, deriving most of its wealth from sea-related businesses. Shipyards and wharves filled the waterfront, chandleries and sail lofts lined Water Street, and skilled craftsmen were abundant. That coupled with controlling trading routes made it one of America's wealthiest towns. Since then, Castine's remoteness and lack of major fires have preserved what were the homes of wealthy merchants, shipbuilders and sea captains. Thanks to the summer visitors who began buying and preserving these homes in the 1970s, Castine is a time capsule. “That's why it looks like a quintessential New England village on steroids,” Lutts says.
The Penobscot Expedition
Castine may be only a footnote in America's timeline, but it deserves more attention, not only for its forts, but especially for the Penobscot Expedition, America's worst naval defeat prior to Pearl Harbor.
Plan your trip
Location: 137 miles northeast of Portland, Maine, on the Blue Hill Peninsula
Getting there: You can fly into international airports in Bangor, about a one-hour drive to Castine; Portland, a little more than two and a half hours away; or Boston, about a four-hour drive. You can also get to Castine by private or charter boat or aboard American Cruise Lines’ Maine Coast and Harbors Cruise.
Best time to visit: Between late May and early October, when museums, accommodations and restaurants are open and interpretive signage is in place. Depending upon your level of interest in forts, battles and architecture, you can spend anywhere from a couple of hours to a full day immersed in Castine's history.
Accessibility: Getting around Castine is easy, although those using wheelchairs and walkers will discover that most downtown businesses require steps for entry, and Main Street ascends a hill from the harbor to Fort George.
Where to stay
Slumber in history downtown at either of two classic country inns with lovely gardens: the 1894 Queen Anne-style Pentagoet Inn (from $135 with breakfast) and the 1898 Castine Inn (from $110 with breakfast). Both provide comfortable accommodations with period furnishings and décor, but neither is wheelchair accessible. You'll find hotels with ADA rooms in Ellsworth, approximately 45 minutes northeast.
Where to dine
Mismatched antique china, soft jazz and candlelight set a gentle tone in the Pentagoet Wine Bar (at the inn), with small plates served indoors or on the porch. Try the crab cakes, and trust the sommelier to pick the perfect wine.
In mid-June 1779, British forces arrived in what's now Castine and began building palisaded Fort George out of dirt, manning it with 700 soldiers to defend their lands in Canada and cut off timber supplies to the American rebels. “They intended to establish the province of New Ireland and hold the coast for Britain,” British novelist Bernard Cornwell said in an NPR interview. His novel The Fort tells the story of the fight for the strategic outpost.
Upon learning about the British occupation of its lands, the Massachusetts legislature sent the largest fleet assembled during the Revolution. The Penobscot Expedition comprised 18 armed ships and 21 transports with 900 militiamen and 300 Continental Marines.
It should have been a rout, given that American forces vastly outnumbered the British troops, which were protected only by three sloops in the harbor. Under heavy British fire, 600 American militiamen landed and climbed the cliffs around Dyce Head, claimed the high ground and came within a half-mile of the unfinished fort. Then the expedition fell apart: The general in charge of it wouldn't attack the fort until the sea forces destroyed the British ships in the harbor, but the commodore in charge of those forces wouldn't attack the ships until the general's troops secured the fort. “It's this horrible situation of watching a great ambition being destroyed by sheer incompetence,” Cornwell said.
While the Americans dithered, the British requested reinforcements and kept building. When nine British warships appeared on the horizon, the Americans panicked, abandoned their plans to attack, and retreated at dawn, sailing upriver. The British trapped them and either burned or captured all the American ships.
Forts George, Pentagoet and Madison
Other than a lone cannon pointed down Pleasant Street and a reconstructed stone magazine, only the earthworks remain at Fort George, a seven-acre, town-managed state park listed on the National Register of Historic Places. Walk the ramparts to get a sense of the fort's strategic importance and its size. Gaze down to the harbor and out over Penobscot Bay and imagine trying to arrive undetected to wage an attack against the fort. Also consider the challenge of carrying supplies from ships to the fort.
Today, like many of Castine's historic sites, Fort George is integrated into everyday life, doubling as a softball field. “It's perfect for it; spectators sit on the earthworks and watch the kids play,” Lutts says. When the adjacent nine-hole public golf course opened in 1897, golfers teed off from Fort George's ramparts. That tee has been moved, but golfers still play in and around another fort's redoubts.
Look for two other waterfront forts along Perkins Street. A wooden cross marks the site of Fort Pentagoet, dating from 1635. In the 1980s, archaeologists excavating here unearthed a copper plate from a 17th-century French mission, Our Lady of Holy Hope, the name of the adjacent Catholic chapel.
The U.S. Army constructed Fort Madison in 1808. Union forces rebuilt and garrisoned it in 1863. You'll find Civil War-era earthworks and a lone cannon on this open grassy site with spectacular views of boats to-ing and fro-ing across Penobscot.
Once you've discovered the forts, take in some of Castine's other historical sites on a self-guided tour by pairing the widely available Historic Castine Walking Tour brochure (free) with the historical society's excellent Castine History Highlights app. Both complement interpretive signage throughout town detailing skirmishes, forts, battle sites and incidents. (Not all signs, created between 1910 and 1920, are accurate, so trust the app for correct info.) Main Street will charm you with its period homes, historical inns, and handful of independent shops and galleries; American elms, a species that flourished in the U.S. before Dutch elm disease arrived in 1921, edge the street. “Castine has more than 300 majestic elms. It's rare to find so many in one place,” says Julie Van de Graaf, keeper of the Pentagoet Inn.
Prefer a guided tour? From mid-June until early October, take one of the historical society's free (donations appreciated) walking tours covering about a half-mile and lasting just over an hour. The forts aren't included, but you learn about the Penobscot Expedition and some of Castine's intriguing but little-known history. For example, the two unmarried Hawes sisters ran a home-based, 19th-century school for boys. Despite never having been to sea, the women taught navigation and higher mathematics to Castine's future sea captains.
To cover more territory, opt for one of Castine Touring Company's 60- to 90-minute tours (207-801-1122, suggested donation $10 per person) aboard a five-passenger, street-legal golf cart, a good choice for those with mobility restrictions. You'll see the forts, Dyce Head Lighthouse and the Maine Maritime Academy campus, as well as historical houses and churches.
After touring, drop in to two engaging museums that defy their small-town locations.
At the Castine Historical Society Museum, an informative exhibit on the Penobscot Expedition explains the rout and the roles of key players, such as Paul Revere. Marvel at 300- to 500-million-year-old trilobite fossils at the Wilson Museum, which showcases early 20th-century geologist John Howard Wilson's impressive collections, including local history.
The adjacent Georgian-style Perkins House (tours 2-5 p.m. Wednesdays and Sundays in July and August, or by appointment; $5 per person) serves as an especially fine example of colonial architecture dating from 1763. You'll see Perkins family portraits and heirlooms, along with artifacts from other prominent figures in Castine's history.
Making this seaside village even more inviting are friendly locals. “History and architecture draw visitors to town, but many of our guests return because they fall in love with the warmth of our community,” Van de Graaf says. She recommends attending Castine's summer outdoor concerts, noting that the town's all-ages community band performs on the Fourth of July and some Friday nights.
Other things to see and do
Boat tours: You'll best appreciate the town's strategic location from the water. Sail for two hours aboard a 1934 motor-sailor with Guildive Cruises, or go paddling on a two- to six-hour kayaking tour with Castine Kayak Adventures.
Castine Post Office: Built as a customs house in 1817, the country's second-oldest continuously operating post office has handled the mail since 1833. See its brass mailboxes and Victorian-era gas lighting fixtures, since electrified.
Dyce Head Lighthouse: A path leads to this 1828 beacon.
Maine Maritime Academy: Founded in 1941, it's now one of the country's six state maritime academies.
Witherle Woods Preserve: An old carriage road and hiking trails lace Witherle Woods Preserve. The trail map notes a hilltop lookout used by the British as well as three batteries, one dating from 1779 and two from 1814.
Nearby forts: In an easy day trip from Castine, see both Fort Point State Park, home to earthworks of 18th-century British Fort Pownall, and Fort Knox, a sprawling granite fort dating from 1844.
Insider tip: Watch the sunset over the Atlantic from Backshore Beach. “You're looking west over Penobscot Bay, and the setting sun can turn the waters golden pink,” Van de Graaf says.