Portland, Maine Vacation Guide

Deering Oaks Park

Autumn colors at Deering Oaks Park in Portland, Maine.

 Portland | Old Port | Arts District | Recreation | South Portland | Directory | Map

Mainers are not normally known for their humor, but they like to say the good thing about Portland is that is it so close to Maine. Why do they say this? In comparison to the rest of the state, Portland looks and feels like another world. Portland has a cosmopolitanism and urban flair that is absent throughout the rest of Maine, and it seems to be getting hipper every year, being a haven for brew pubs and cafes, a noteworthy arts and antiquing destination and up and coming foodie hotspot (actually, the artisan food and charcuterie has already arrived, and now people are coming in droves). Maine’s foodie hotspot has turned into an Epicurean sunspot, and after a walk through the Old Port and Arts District, you cannot help but be blindingly aware that Portland has worked hard to cement its reputation as a distinguished food destination. Who would have thought that in a densely forested, sparsely populated, remote corner of the northeast there would be an enclave of master chefs who rival the culinary experts of Spain, France and San Francisco? Portland is a small city with world-class ideas and an entrepreneurial attitude.

The Portland Character

Situated on a three-mile peninsula, Portland is Maine’s largest city. The Portland Jetport, a small international airport, is located five miles out of town. There are roughly 64,0000 residents in the greater metropolitan area. While this might be large by Maine’s standards, Portland is a compact and walkable city. In other words, it is like a big small town, and in that respect it is not unlike Boston, a city that it is often favorably compared to.

The fishing industry and working waterfront are still the heart and soul of this small community. In Portland, the traditional and historic Maine runs parallel with a more youthful, trailblazing, Brooklyn neighborhood cultural vibe. In essence, it is this far-ranging diversity and opposites attract mentality that gives Portland its defining character. Metaphorically speaking, the big small town is like a seafood bouillabaisse or a fisherman’s chowder. Organic gardeners and holistic environmentalists happily coexist with grizzled fishermen and ship builders. Brooks Brothers yuppies sit side by side at the craft beer pub with Jack Kerouac style hipsters. At the end of the day, the tranquil and pleasant way of life that is found in Portland, which numerous U.S. magazines have commented on (accolades coming from both U.S. News and World Report and Bon Apetit) is the result of a tightly-knit community that works together to give Portland a unique sense of place and a spirited identity.

The Old Port

A proud working harbor and an international hub since the 17th century, Portland’s commercial waterfront is the first thing you see as you enter town on the Maine Turnpike. A quick glimpse of the fishing vessels, oil tankers, luxury yachts, barge cranes, whale-watching boats, cruise ships, skiffs and schooners is enough to suggest the type of cultural and recreational variety you will find in Portland. In other words, do not be surprised to see lobstermen in hip waders working right next to the dock where ferries usher suntanned and sandaled tourists to Casco Bay’s Calendar Islands.

The Old Port refers to the warren of cobblestone streets that begin at Commercial (which parallels the water) and twist past the brick buildings, refurbished Victorian warehouses and old ship chandleries. In the old days, candle makers and sail stitchers occupied this side of town, and after the fire of 1866 the entire area was rebuilt with brick. Today, these buildings house art galleries, trendy boutiques, cheese shops, independent bookstores, watering holes and locally sourced restaurants. Chain stores are at a minimum in the Old Port.

The Old Port is comprised of four main streets: Market, Exchange, Middle and Fore. Similar to pedestrian-friendly Church Street in Burlington, Vermont, this area of Portland has a lively street fair type of atmosphere. In the summer, the Old Port is the ideal place to shop, quaff a cappuccino and do some people watching. However, why not mix up the drinking, five-star dining and endless appetizing with a couple of the Old Port’s top attractions?

The Portland Fish Exchange and the Harbor Fish Market provide a full-sensory peek into New England’s most famous and dynamic industry. There are lively lobster pens and coolers of cod, flounder and monkfish. Haggle a price for dinner while you watch the fishermen prepare their nets and clean their gear. The Harbor Fish Market, a Portland institution, has been shipping fresh seafood all over the globe for the past forty years. If life on the wharf is not your thing, then visit the Maine Narrow Gauge Railroad Co. and Museum. First, enjoy the collection of old locomotives that are housed in the museum, and then take a three-mile tour along Casco Bay on a traditional gauge railcar.

The Arts District

Extending from the top of Exchange Street to the Portland Museum of Art, the Arts District is the city’s main artery. Congress Street is at the heart of the district, and it is lined with a wealth of galleries, specialty stores and restaurants. On one end of Congress you will find the Merrill Auditorium, which is the home of the Portland Symphony Orchestra, while the other end of the street is anchored by the Portland Museum of Art, which was designed by I.M. Pei and is considered one of the premier museums in New England. Most of the city’s top attractions and must-see highlights can be found in the Arts District. From the Children’s Museum and The Portland Harbor Museum to the Longfellow House and the Victoria Mansion, park the car and get out and explore.

Greenery, Recreation and Other Places of Note

According to Organic Gardening magazine, Portland is one of the nation’s greenest cities, and this title makes sense considering Portland is often referred to as The Forest City. To the west of downtown Portland, you will find Deering Oaks Park. This beautiful, 55-acre public spread has hiking and biking trails, a baseball diamond and tennis courts. There is also a pond that becomes a popular ice-skating destination in the winter. However, the real jewels in Portland’s environmental crown are the eastern and western promenades. Locals with tell you that the western promenade is a tourist magnet, so pack the picnic basket and head to the other end of town. The eastern promenade is a 68-acre hillside park. At the bottom of the hill, you will find both the Eastern Prom Trail and the East End Beach. The promenade is an idyllic place to spend a summer afternoon. Crescent Beach State Park, Two Lights State Park and Fort Williams Park can also be found in the nearby area.

Vacations are all about finding the perfect view. The Portland Observatory, which was built as a signal tower in 1807, is the type of place where you will want to take out your camera, point, zoom and snap… over and over again. There is a museum at the base of the observatory (spoiler: this is the last signal tower in the U.S.) and then a series of stairs lead up to the Orb deck. You will be treated to a birds-eye view of Portland, Casco Bay and the White Mountains.

South Portland

Unfortunately, South Portland gets a bad rap. Neither fitting into Portland’s hardscrabble life at sea image or the pioneering Cool as a Organic Cucumber vibe that dominates the Old Port and Arts District, South Portland is like the black sheep of the greater metropolitan area. The Maine Mall is the vortex of this area, and the city’s chain stores, suburban sprawl and rampant commercial development seem to pinwheel out from the behemoth shopping complex. Seriously, every city needs retail stores and they have to exist somewhere, right? Distinct neighborhoods are what create a multi-faceted and user-friendly city. While most visitors fail to get beyond the Maine Mall parking lot, South Portland also has an attractive downtown and a network of green spaces. Willard beach and Spring Point Ledge Light can also be found in the area. Considering South Portland is the home of 23,000 Mainers and the fourth-largest urban area in the state, it is certainly worth a look.

Stay a Day, Spend a Weekend

Portland has burned to the ground twice. First, the British torched the city in 1775. Then, in 1866 (and known as the Great Fire) over 1,500 buildings were destroyed when a firecracker landed in a pile of wood shavings. Throughout the years, Portland has also been known by other names, being called both Casco and Falmouth at one point or another. What is the underlining theme of this abbreviated history lesson? Portland knows how to reinvent itself. Today, it is experiencing an unparalleled Renaissance. Foodies, history buffs, art enthusiasts, nature lovers, aquatic aficionados, hipsters and retirees are exiting the Turnpike or landing at the Jetport for a variety of cultural or recreational reasons. Some spend a day, others spend a weekend and a few will move to Portland permanently. When Vacationland turns into a permanent residence, you know a big small town has a good thing going.

Portland Area Directories

Visit the following directories to find lodging, dining, attractions, shops, services and recreational activities in the Portland, Maine area.

Portland Maine Map

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