Take a leisurely day’s drive along the route, or plan for several day-trips to explore stops along the route.
We begin in Old Orchard Beach, along Route 9, where the historic pier and amusement park harken back to a simpler time in our past. Horseback riding with Carousel Horse Farm along the beautiful seven-mile beach is a remarkable way to view the coastal fall colors.
From Old Orchard, head south on Route 1 to Route 112 driving west to Hollis Center, then north on Route 35 through pastoral landscapes to Standish. During the War of 1812, Portland bankers hid money from the British in the Daniel Marrett House; today, you can tour this 1789 Georgian mansion in Standish, which is filled with furniture and memorabilia from the 18th and 19th-centuries.
Take Route 25 to Portland, a place that native son, Henry Wadsworth Longfellow, called his “jewel by the sea.” Most people who are familiar with this gem of a city agree that his 19th-century sentiment still rings true today. As one of the Northeast’s most sophisticated small cities, Portland pulses with a delightfully vibrant urban atmosphere, yet retains all the warmth and charm of a close-knit community. Per capita, Portland is said to be home to more places to dine than any other American city, save San Francisco; the caliber of the fare to be found here has been noted in Bon Appetit, Travel & Leisure and Wine Spectator. Portland also maintains a thriving arts tradition, evidenced in its many galleries, theater and dance companies, performance halls and museums.
Built on a peninsula, Portland is bounded by island-studded Casco Bay, placid Back Cove and the Fore River; such geographic constraints led to the happy solution of building the city up rather than out. The resulting urban landscape consists of tall and stately brick, granite and brownstone buildings in an array of 19th-century architectural styles. Portland is a wonderful city to explore on foot; Greater Portland Landmarks offers walking tour maps of the city’s four main historic districts.
Shop and dine in the brick-and-cobblestone Old Port District. Climb to the top of the newly renovated Portland Observatory, a fixture used to alert merchants and townspeople of ships arriving to port in the 18th and 19th-centuries.
From Portland, head south on Route 77 to Southern Maine Community College in South Portland, where the Spring Point Light rests on a breakwater adjacent to the Portland Harbor Museum, which features as its centerpiece the bow of America’s last clipper ship, the Snow Squall. This 157-foot beauty was left to rot in South America in 1864, but portions of the vessel were recently recovered and are being restored at the museum.
Traveling a short distance from Spring Point to Shore Road in Cape Elizabeth, you’ll find fort Williams Park, offering heart-stopping views of the sea and access to world-famous Portland Head Light. Commissioned by George Washington in 1791, this light enjoys a long and fascinating history, and has spawned its fair share of legends. A local favorite dates to the early 1900’s, when the lighthouse-keeper’s parrot (who reportedly cursed like a sailor) acted as a barometer, telling the keeper to turn the light on when a storm was approaching. Henry Wadsworth Longfellow also visited the light frequently, and is said to have penned some of his poetry here. Learn more about this landmark beacon at the museum housed in the former lighthouse-keeper’s quarters.
Just a few miles south on Route 77 you’ll find Two Lights State Park and another of the region’s famous lighthouses painted by countless artists, including Andrew Wyeth. While there, sample authentic Maine cuisine at a lobster shack with an unparalleled view of the Atlantic.
Follow Route 77 to its end and turn left onto Black Point Road to visit Scarborough Beach State Park. Stop to soak up some sun and frolic in the surf. Further down this neighborhood road is Prouts Neck, home of revered painter, Winslow Homer. An unmarked trail beginning at Winslow Homer Road winds along the cliffs where the artist was often inspired.
Head back on Black Point Road and take a right onto Route 1. Follow the signs to Route 295.
Take Route 295 North through Portland and make a stop at the Delorme Mapping Company in Yarmouth, to experience Eartha, the world’s largest globe as listed in the Guinness Book of World Records. Continue north on Route 295 to the shopping mecca of Freeport, home to legendary L.L. Bean and a multitude of other brand-name outlet stores.
After your Freeport shopping extravaganza, head back down Route 295 to Route 95. Continue south on 95 to Route 302 to North Windham and the lower portion of the Sebago Lakes Region. Here you can explore shops full of authentic Maine crafts and snoop around the old antique haunts that give Route 302 its nickname of “Antique Alley.” Follow Route 35 south into Standish, bearing right onto Route 25 West. In Standish, you can stop at roadside farms and pick some of the crispest apples in the state.
Traveling west along Route 25 brings you to Kezar Falls. Take 25 West to Porter, site of the Porter Covered Bridge.
Continue south on Route 160 to Limerick, and then head west on Route 11 to the Victorian village of Willowbrook in the town of Newfield. This gem of an historic site shouldn’t be missed; made up of over 37 buildings (including several homes, a ballroom, schoolhouse, restaurant and ice cream parlor), the village was carefully restored after it was destroyed by fire in 1947. Even the details transport you to an earlier era; artifacts include horse-drawn carriages, vintage toys, Victorian clothing and an 1894 carousel.
From Newfield, continue on Route 11 South to Sanford. Take Route 109 to South Sanford and turn right onto Route 4. Follow Route 4 to Route 236 in South Berwick. From Route 236 take a side trip east on Route 91, where you can take a tour of the 1787 Hamilton House ;(open until Mid-October), widely regarded as one of Maine’s finest manor homes. Its Georgian architecture is stunning, and the interior is decorated with exquisite period furnishings. In addition, musical performances often take place on the house’s lovely grounds.
Proceed south along Route 236 to Route 1 in Kittery where popular outlet stores make this a key stop for shoppers. Kittery is also home to the historic community of Kittery Point, which served as a vacation destination for many respected 19th-century artists and writers, including Samuel Clemens (Mark Twain). It was Clemens and a group of other seasonal residents that decided to preserve the charm of this part of the world by purchasing several historic buildings in nearby York, America’s first chartered city (1642).
Head north on Route 1 from Kittery to Old York Village, where a number of these buildings are open for tours. Among these is the Old Gaol, a prison dating back to 1719 and believed to be the oldest remaining public building of the English colonies. If you’re interested in gravestone rubbing, don’t miss the old Burying Ground, where stones bear the Old English spellings of 18th-century town members. Also of interest is York Village’s Civil War Monument; upon inspection, you’ll notice that the soldier is wearing a confederate uniform. Due to a shipping mistake, York’s statue is on display somewhere south of the Mason-Dixon Line.
While in York, explore the village of York Beach, where Victorian-era shops line the boardwalk at Long Sands Beach. Soak up some sun and stop at the village’s restaurant and taffy shop, which has been owned by the same family since 1896. In addition, make sure to visit the circa-1879 Cape Neddick (Nubble) Light; Sohier Park makes for a very scenic picnic spot, overlooking the light.
Drive north on Route 1 from York to Ogunquit. This seaside village’s heralded natural beauty drew artists from near and far in the 1800’s, making it one of the nation’s first art colonies. Among the many artists who found inspiration here were Maurice Prendergast, Walt Kuhn and Edward Hopper. Their legacy lives on today in the exquisite galleries and museums that line the village’s quaint streets and scenic coves.
If you take this tour early in the season, take a stop at the Ogunquit Museum of American Art (closes at the end of September); a museum dedicated exclusively to 20th-century American art. In addition to housing over 1,300 significant paintings, sculptures, drawings and prints, the museum’s location overlooking the Atlantic is truly breathtaking, inspiring a former Director of the Metropolitan Museum of Art to deem it “the most beautiful small museum in the world.”
While in town, take a walk on Marginal Way, a footpath offering amazing views of the sea as well as of the summer cottages that line the shore. The path ends at Perkins Cove, a picturesque harbor surrounded by galleries, restaurants and boutiques.
If you’re touring the area at the beginning of September, don’t miss Capriccio, Ogunquit’s Annual Week Long Celebration of the Arts. This culminates in the Festival of Kites, right on the beach. Colors take wind, as kites of every size and description fill the skies over Ogunquit Beach.
Continue north on Route 1 to Wells, where you’ll find 7 miles of wide, sandy beaches, antique shops and the Laudholm National Estuarine Research Reserve. This 1,690-acre reserve and historical farmhouse houses the Maine Coastal Ecology Center, and offers seven miles of trails showcasing the season’s foliage.
At Wells Harbor Park, enjoy free concerts (during the summer) at the Hope Hobbs Gazebo, take a moment to reflect on life at the prayer bell dedicated to those who perished on September 11 or take in one of the many festivals held each year.
Wells offers many historic and picturesque points of interest. The Schoolhouse Division No. 9 offers a unique look at school life in the early 1900’s. Built on one-half acre of land for a total cost of $878.72, it was designed for a lone teacher to instruct 35 to 40 pupils from kindergarten through grade 8. The Museum at the Historic Meetinghouse on Route 1 includes artifacts and memorabilia of early Wells and Ogunquit life as well as an extensive genealogy library of the towns’ early residents. Throughout Wells there are many monuments marking important historic events such as the first home built in Wells (1641).
Head north on Route 9 to Kennebunkport, a charming coastal village that was plunged headlong into worldwide fame when summer resident, George Bush, became President in 1988. Take a scenic drive along coastal Route 9 to catch a glimpse of the Bush mansion on beautiful Walker Point, as well as the other magnificent summer homes that grace the shoreline.
Watch handcrafted beer and ales being brewed just steps away from the exciting dining and shopping area at Dock Square, in the town’s center.
Don’t miss nearby Kennebunk (just up Route 9A), where you can take a tour of the Brick Store Museum on Main Street, an impressive three-building complex that houses local memorabilia, fine art, antique furniture and nautical exhibits. Take time to visit the historical White Columns home (built in 1853), which offers an incredible tribute to the Victorian era: one of the stipulations given by the former owner when the home was bequeathed to the historical society was that nothing in the house be changed. This, apparently, had been a ‘house rule’ for some time before that. The home features its original wallpaper, carpeting and furnishings.
From Kennebunkport, take Route 9 North through Biddeford/Saco, where a diversion to the York Institute on Main Street in Saco is a fascinating trip through Maine’s past. The Institute is one of Maine’s oldest museums, and features an exceptional collection of Federal period furnishings and painting, glass, textiles and other rarities from 18th and 19th-century Maine families.