Cities/Towns

In Bangor, the 31-foot statue of legendary lumberjack Paul Bunyan still stands tall over what was once the “Lumber Capital of the World.” In the 1830s, the city was home to more than 300 sawmills, and the Federal-style mansions constructed during the lumber boom still stand in the Broadway region. Horror novelist Stephen King resides in this neighborhood, and many scenes from his books and movies were taken from actual sites in Bangor.

Bar Harbor, Mount Desert Island’s largest community, was New England’s premier summer resort in the 19th century. It was home to the largest hotel in North America and to Millionaires’ Row, a line of spectacular summer estates built for America’s most powerful families—Rockefeller, Ford, Vanderbilt, Carnegie, Astor and Morgan, to name a few.

Freeport is located along the shores of upper Casco Bay, approximately 20 minutes north of Portland. It is best known for its upscale outlet shopping and as home to the world-famous L.L. Bean outdoor store. Locally owned shops offering Maine-made items can also be found throughout the downtown area. However, Freeport isn’t all about shopping. The historical town is often credited as being the birthplace of the State of Maine. Many of the meetings leading up to the state’s separation from Massachusetts in 1820 took place in Freeport’s Jameson Tavern, which is still in operation today. A good number of the town’s original schools, homes, and churches have been preserved and refurbished, thanks to a very active historical society. The town’s dedication to historic preservation has also ensured that the old blends nicely with the new. Even the local fast food restaurants have a distinctively New England feel.

Kennebunks are chock-full of fine dining establishments and high-end accommodations. However, you can still find moderately priced places to stay with a little planning, and some of the best spots to dine are low-key lobster pounds where great food at a good price can be had. Boutiques, some with sister locations in exclusive Palm Beach, Fla., line the streets. Visitors will enjoy taking the scenic drive along Ocean Avenue, which runs along the Kennebunk River to the ocean. The route provides equally stunning views of the Maine coastline and the palatial homes of Kennebunkport’s rich and famous, including the summer retreat of the 41st U.S. President George Herbert Walker Bush.

Portland, located on Casco Bay, is Maine’s largest city as well as its creative hub. Many craftspeople, artists, and other creative types have chosen to live and work here, positioning the city as one of the most fashionable locations in the Northeast. Portland’s Old Port, constructed in the 1800s, has been converted into a first-class shopping and dining district.