Off-Season City Getaways
Warm beaches and fall foliage are nice, but Greater Portland also wears the "quiet season” well with a shimmering urban landscape that warms the soul.
Don’t let Portland’s small size deter you - urbanites will find the region’s off-season replete with fine dining, culture, sports, and an abundance of arts and entertainment. The most cultured cityphile will be amazed at all that’s going on, and even more pleased upon discovering the metro area’s ease and value compared with larger downtowns.
Imagine escaping for a weekend to Maine’s cultural hotspot. You dine at a James Beard award-winning restaurant, take in a touring Broadway show, followed by a late-night cocktail, then are shuttled to your luxury hotel in Portland’s historic downtown. You wake to a day of museums, culinary tours, and shopping with the symphony, opera, ballet, or headline concert for a nightcap. Perhaps you linger over a relaxed brunch, then cheer on a professional baseball or basketball team at a home game. Or hop a ferry and see lighthouses and forts on your way to an island for lunch, then catch the train to shop all night in Freeport.
With our small-scale accessibility, visitors from other cities will be surprised at how much more they can see and do over the course of a weekend in Greater Portland than if they experienced similar activities in their own cities…then elated to discover spending far less! Yes, even with the additional gas, train, or plane fare, Portland is a winter bargain escape.
So imagine exhaling, relaxing, living well, and having fun with less aggravation and cost than if you’d stayed home. Portland isn’t just for summer anymore!
Architectural Eye Candy
Portland’s preservation ordinance protects landmarks and designated historic districts, ensuring a city whose past is glimpsed daily, even as it embraces the present and prepares for the future.
At the heart of Portland’s visual appeal is an historic urban hub rich with architectural gems. Because a 4th of July fire in 1866 destroyed most of the city’s commercial buildings and homes, much of the city’s historic architecture dates from the Victorian era. Well-preserved examples of 19th century styles dot the landscape, co-existing comfortably with more modern buildings.
To best explore Portland’s historic neighborhoods, take a seasonal guided walking tour with Greater Portland Landmarks, or a self-guided walking tour using the interactive maps and downloadable pdfs on their website (portlandlandmarks.org). You can also purchase printed walking tour booklets from the Visitor Information Center at Ocean Gateway. Viewing building details such as graceful cornices, granite and brick facades, and delicate gingerbread trim is best done on foot; pedestrians can walk the length of the Portland peninsula in under an hour and see a wealth of architectural styles.
One of the few buildings to survive the devastating fire of 1866 is the Portland Observatory. Built in 1807 as a way for commercial ship owners to know when their vessels were entering the harbor, this 86’ octagonal tower is one of the only remaining wooden maritime signal towers in the country. Its unique profile is one of the defining features of our coastal city, and the views after climbing its spiral staircase are spectacular and panoramic.
If you can’t get enough of historic architecture, you can stay at an historic bed and breakfast decked out in antiques, some with operating fireplaces in the parlors and rooms. The Inn at St. John (1897) is the oldest continuously operating Victorian hotel; comfortable rooms with period details are a bargain find if you don’t mind the lack of an elevator. Also on the peninsula, the Portland Regency is a fullservice hotel housed in a late 19th century armory, a marriage of historic sophistication with modern amenities.
Greater Portland is also steeped in history and oozing visual appeal. On a drive along Shore Road in Cape Elizabeth, you’ll see brick, stone, and wooden mansions that overlook the sea. Route 88 in Falmouth and Cumberland Foreside is also lined with stately homes. Yarmouth and Gorham exemplify traditional New England villages with distinct town centers surrounded by lovely houses. Freeport’s downtown has become a world-renowned shopping destination with many boutiques occupying historic buildings; even the Freeport McDonalds is a tourist destination, located as it is in an historic village home.
Taking a spontaneous beach trip? Hitting the road for a scenic leaf-peeping drive? Portland is happy to accommodate last-minute visitors. But to ensure the comfortable stay of your choice, we recommend that visitors make reservations before they arrive in Maine. Room availability can be limited, especially during the peak summer and fall seasons, and accommodations often fill in advance, especially in the Old Port and downtown areas.
PACKAGES & DEALS
If visitors miss an opportunity to stay downtown, there are outstanding hotels, motels, and inns just outside of the city. Visitors may look to Freeport, Westbrook, Cape Elizabeth, South Portland, Old Orchard Beach, Yarmouth and Kennebunkport. A city in the heart of vacationland is certain to have a choice of vacation packages and deals for visitors. Groups, couples, holiday shoppers, and weekday travelers will find stay (and play) packages throughout the year. Consult individual properties or sites, or see our Deals & Packages section to find a special package that suits your stay.