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Historic Maine Driving Itineraries

Maine Preservation created these historic tours to celebrate Maine’s bicentennial in 2020 by featuring pre-statehood places and the people who forged early Maine with conveniently mapped out trips. Explore Maine’s cultural and architectural roots as you travel by some of the state’s best examples of mid-18th- and early-19th-century architecture.

The tours are organized by region and range from 30 minutes to four hours of exploration. On your way, be sure to experience some of Maine’s beautiful and historic downtowns, many of which are nationally accredited Main Street communities and are vibrant places to find local food, shops, cultural happenings and distinct New England architecture. We recommend giving yourself plenty of extra time to take in the sights and support local businesses along the way!

Southern  Maine Coastal Region tour 

This tour goes from Cape Elizabeth to Biddeford, and you’ll stop to visit the iconic Portland Head Light, built circa 1790. During the warmer months, you can grab a bite to eat from food trucks like Bite Into Maine. This tour also includes the Richard Hunniwell House, built in the early 18th century, it’s one of the oldest surviving houses in the state.

Maine’s Lakes & Mountains Tour

On this tour through Maine’s Lakes and Mountains, stop and see the Churchill Bridge (built circa 1797), a dry-laid, rubble stone structure. It’s one of only three lintel bridges left in Maine. The Leavitt Hardware Store in Norway was built by William Cox in 1816 and today is the perfect spot to enjoy some gelato at Dolce Amici.

Greater Portland Tour

Visit a centuries-old cemetery in New Gloucester and see other fantastic examples of architecture on this tour through the Greater Portland and Casco Bay Region. One property on the tour – the Bagley Bliss House – is now a bed and breakfast! Try to find the oldest grave you can in the Lower Corner Cemetery in New Gloucester – the first burial was in 1754.

Midcoast Tour

Head to MidCoast and see meetinghouses and an old fort on this tour through Bristol down to Westport. Visit the museum in the Harrington Meeting House in Bristol. There is no charge for entrance to the museum, however a donation is appreciated. During July and August, it is generally open to the public on Monday, Wednesday, and Friday afternoons from 2 until 4:30 PM, with volunteer docents in charge. The blockhouse at Fort Edgecomb with its octagonal shape is quite unusual, and the fort is open to the public. Enjoy an overnight stay at the Squire Tarbox Inn, in a Federal style dwelling. constructed in 1763.

Kennebec Valley/Central Maine Tour

The tour through the Kennebec and Moose River Valley Region offers you a chance to visit the Blossom House, built circa 1808, now the Monmouth Museum, open to the public in the summer. Another home-turned-museum on this route is the Redington Museum for the Waterville Historical Society.

Maine Highlands Tour

Head to the  Maine Highlands on this tour and see the Robert Carleton House, one of the oldest surviving buildings in Piscataquis County. It is a significant example of a late Federal-style structure. This tour ends in Aroostook County in Houlton, home to Pluto in the Maine Solar System Model, the largest 3-D scale model of the solar system in the western hemisphere. Continue north to Presque Isle to see the solar system in its entirety!

DownEast and Acadia Tour

On this tour through the DownEast and Acadia Region, you can visit the Ruggles House Museum seasonally. The house, built in 1818, has been a museum ever since 1951. In Machias, you can visit the Burnham Tavern Museum in one of 21 homes designated as most significant to the American Revolution.

There are 26 tours in total to enjoy throughout the many unique regions in Maine. You can see homes built in the 1700s, when Maine was still part of Massachusetts and under British rule, like the Thomas Perkins House in Kennebunkport or the McCobb-Hill-Minott House in Phippsburg.

While many of the houses are privately owned, some have been turned into museums, like the Wadsworth-Longfellow House in Portland, which was the childhood home of the poet Henry Wadsworth Longfellow, or the Holmes-Crafts Homestead in Jay, which is part of the Jay Historical Society and available for tours by appointment.

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