Begin in Kittery, where a multitude of popular outlet stores makes this a key stop for shoppers. Kittery is also home to the historic community of Kittery Point, which served as a summer destination for many respected 19th-century artists and writers, including Samuel Clemens (Mark Twain). It was Clemens and a group of other summer 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 from 1719 and believed to be the oldest remaining public building of the English colonies. If you are 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, visit the local amusement park and zoo, and stop at the village's restaurant & 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; the beacon's grounds make for a very scenic picnic spot. Before leaving York, take a side trip west on Route 91 to South Berwick, where you can take a tour of the 1787 Hamilton House, 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.
Head up Route 1 north from York to Ogunquit. This seaside resort's heralded natural beauty drew artists from near and far in the late 1800s, 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.
Of special note is the Ogunquit Museum of American Art, 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, and which features a draw footbridge across its entrance.
For a unique way to see the sights, hop on one of Ogunquit's old-fashioned trolleys - complete with brass, wood and leather detailing.
Also make sure to enjoy the white sands of three-mile-long Ogunquit Beach, recently rated one of the ten best beaches in the U.S., and take in a show at the Ogunquit Playhouse, a grand old summer-stock theater first opened in 1933. The Ogunquit area also offers a number of exquisite inns, many within walking distance of the beaches and attractions around town.
Head north on Route 1 to Wells, where you'll find wide, sandy beaches, antique shops and the Rachel Carson Wildlife Refuge, which provides habitat for over 250 species of birds. Continue on Route 1 north 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.
Enjoy a stay at one of Kennebunkport's stunning inns, one of which houses a four-star restaurant that has received national acclaim. Many inns and B&Bs are located just steps away from the exciting dining and shopping area at Dock Square in the town's center.
In the equally lovely sister town of Kennebunk (located due west on route 9A), take a tour of the Brick Store Museum, a wonderful three-building complex that houses local memorabilia, fine art, antique furniture and nautical exhibits. And, right up the street is the historical White Columns home (built in 1853), which offers a wonderful 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, head north on Route 1 to Old Orchard Beach, where the seven-mile sandy beach is a haven for sunbathers and sand-sculptors (a sandcastle competition draws aficionados from near and far each August). In addition, Old Orchard's historic pier and amusement park offer hours of fun for families. Make sure to take a ride on the old-fashioned carousel, which dates to 1906 and features hand-painted wooden horses.
From Old Orchard, head west on 112 to Hollis Center, then north on Route 35 through pastoral landscapes to Standish. During the War of 1812, Portland banks hid money from the British in the Daniel Marrett House; today, you can tour this 1789 Georgian mansion, which is filled with furniture and memorabilia from the 18th & 19th centuries.
Continue north on Route 35 to North Windham, then take Route 302 west to Naples. Situated on the shore of beautiful, 45-square-mile Sebago Lake, Naples has long been a popular destination for summer visitors. After a canal was constructed between Portland and Naples in 1830, visitors could access Sebago Lake by boat all the way from Boston. Ease of transportation and the desirability of the lake -which features water so pure, Portland still uses the lake for its water supply -gave rise to numerous lakeside summer homes, camps and resorts in the early 1900s.
Although modes of transportation to the region have changed (the canal is now defunct), the popularity of the lake has not: Sebago Lake remains one of the State's most visited destinations, especially for families with children. Visit Sebago Lake State Park and enjoy the white-sand beach, crystal-clear lake and picnic & camping area. Or, for a longer visit, stay at one of the grand old lakeside resorts or summer cottages. While in Naples, board the Songo River Queen, a 90-foot paddle boat offering scenic cruises on Long Lake and across Brandy Pond, through the surviving locks from the old canal, to the winding Songo River. Passengers are often rewarded with deer, moose and loon sightings.
From Naples, continue north on 302 to Bridgton, where you can ascend Pleasant Mountain via Shawnee Peak Ski Resort's chairlifts to mountain bike, hike and enjoy magnificent views of the area's fifty lakes. Head north on 302 from Bridgton to the intersection of Route 117.
Take 117 north to South Paris and take a side trip to West Paris, a charming little town that draws over 90,000 visitors per year. The attraction? Perham's, a gemstone shop that has displayed locally mined amethyst (a large amethyst deposit was discovered in Maine in the 1970s), tourmaline and topaz since 1919. Visit this little wonder of a shop to admire its sparkling wares and get some tips on rock-hounding - you can even get a map to one of the local quarries, where you can do some treasure-seeking of your own.
From South Paris, head north on Route 26 to Bethel, a classic New England village, complete with a village green, stately clapboard homes and a community of friendly locals. Thanks to the induction of train service in 1851, this sleepy mountainside town gained almost instant notoriety as a haven for the city-weary. Grand resorts, hotels and spas offered fresh air, exercise and the promise of better mental health to urban dwellers from Montreal, New York and Boston.
Some of these elegant hotels remain, and offer wonderful respite for the visitors of today. Beautiful inns in Bethel proper as well as the Sunday River Ski Resort just outside of town provide wonderful hiking, biking and golf opportunities amidst some of the most breathtaking mountain views in the East.
While you're in Bethel, make sure to explore nearby Grafton Notch State Park (take Route 2 east, then Route 26 north), where you can take short but worthwhile hikes to Screw Auger Falls, Mother Walker Falls and Moose Cave. In addition, the nearby White Mountain National Forest offers several spectacular hikes to scenic overlooks of the surrounding region. Also take note of nearby Newry's covered bridge (which has been the subject of so many drawings and paintings, it is locally known as the Artist's Bridge), which is a great spot to swim and picnic.
From Bethel, take a scenic drive through one of the most spectacular mountain passes in New England: take Route 2 west to Gilead, then head south on 113 through the White Mountain National Forest to Evans Notch, which offers magnificent panoramic views of the White Mountains.
In Stow, take a scenic side trip by heading east around Kezar Lake, a breathtaking lake nestled at the foot of the Presidential Range. Once back in Stow, head south on 113 to historic Fryeburg, where you can canoe the meandering, sandy-bottomed Saco River on an organized group trip or a leisurely day paddle. While you're in Fryeburg, visit the scenic 1857 Hemlock Covered Bridge.
Continue south on Route 5/113 to Brownfield, then head south on 160 to Kezar Falls. Take 25 west to Porter, site of the Porter Covered Bridge.
Continue south on 160 to Limerick, then head west on 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 Route 109; take 109 east through Sanford to Wells to complete your trip.