The world is huge

Don't miss any of it

Travel news, itineraries, and inspiration delivered straight to your inbox.

By proceeding, you agree to our Privacy Policy and Terms of Use.


Portland, Maine Travel Guide

Portland, Maine is all about lobster. It’s hard to imagine that this crustacean was once deemed poor man’s food, but it’s true — lobsters would wash up on Portland’s shores after a storm and be used primarily as fertilizer and bait. But with the advent of land transportation, lobsters were brought inland by the mid-1800’s, and as the demand for lobsters increased, so did the price. Today, the city boasts numerous restaurants — nearly all of which feature lobster (in some form) on their menus.

But Portland has more to offer than a bunch of crustaceans. The coastal New England port boasts a vibrant working waterfront, an abundance of Victorian-era architecture and numerous historic lighthouses. Nestled on a picturesque seascape, the city is perched on a peninsula jutting out into the island-studded Casco Bay, protected from the Atlantic Ocean. The romantic movie “Message in a Bottle” was filmed in this seaside town, and the famous Portland-born poet Henry Wadsworth Longfellow called Portland a “Jewel by the Sea” in one of his poems.

The historic port was once a major shipbuilding center, as well as one of the busiest fishing ports on the Atlantic as far back as the 18th century. Its success as a port made it a prime target for the British during the War of 1812 and also for the Confederates during the Civil War. The coastline and islands are still dotted with forts that were built to protect the city. Ironically, during an Independence Day celebration in 1866, a firecracker ignited a fire that quickly spread across the city’s east end, destroying 1,800 buildings.

The city quickly rebuilt, resulting in lovely Victorian-era architecture, and today the Old Port (sometimes referred to as the Old Port Exchange) is a bustling seaport with a high concentration of quality eating and drinking establishments. With less than 65,000 residents, Portland is compact enough for visitors to explore the town thoroughly — tourists can stroll along the working waterfront of Commercial Street, walk the cobblestone streets of the restored Old Port district, or visit a historic building or two.

What will you remember most from a visit to Portland? Will it be the lobster traps piled on the wharf, the smell of sea air combined with the chatter of seagulls or a visit to a historic attraction? If you’re like the majority of visitors, a succulent lobster lunch may be your most savory memory of this New England port.

Portland, Maine Attractions

Maine’s oldest lighthouse, built during George Washington’s presidency, Portland Head Light is located on the shores of Cape Elizabeth. Originally, the 80-foot tower was lit with 16 whale-oil lamps. Today there are a number of interpretive displays at the onsite museum.

Climb the 103 steps to the top of the Portland Observatory and enjoy the views of Portland and Casco Bay. This signal tower is the only remaining wooden maritime signal station in the U.S. It was built in 1807 and is currently listed on the National Landmark Registry.

Take a ride on a historic narrow gauge steam train aboard the Maine Narrow Gauge Railroad. Passengers can enjoy the view of Casco Bay while riding along the waterfront by the Portland’s Eastern Promenade.

Originally built in 1858 for a wealthy New Orleans hotelier, the Italian villa-style Victoria Mansion has graceful verandahs, a four-story tower and a lavish interior. The house was named for Britain’s Queen Victoria when it was turned into a museum in 1941. Visitors can tour the property, which still boasts 90 percent of its original contents such as gas light fixtures, elaborate wall paintings and exquisite woodwork.

Built in 1785, the Wadsworth-Longfellow House is the boyhood home of noted poet Henry Wadsworth Longfellow. It was the first wholly brick dwelling in Portland and now features a collection of Maine’s historical artifacts.

Located next door to the Wadsworth-Longfellow House, the Maine Historical Society Museum houses exhibitions that feature art and artifacts that bring Maine history to life, from children’s toys to traditional furniture.

Want to see Portland by bike? Cycle Mania, located a few short blocks from the Old Port, offers rentals by the day or the week.

Take the 15-minute ferry ride aboard Casco Bay Lines from Maine State Pier to Peaks Island. Once there, you can rent a bike from Brad’s Recycled Bike Shop, or take a guided kayak trip with Maine Island Kayak Company to explore the protected waterways of Casco Bay — you’ll paddle past Civil War-era forts, lighthouses and seal-covered ledges.

The Portland Fish Exchange is a fresh seafood auction held Sunday through Thursday at 11 a.m. at the Portland Fish Pier Complex by the Casco Bay Bridge. Commercial fishing vessels are offloaded in the early morning and buyers arrive throughout the morning to inspect the day’s catch. Visitors can watch the auction unfold with the auctioneer soliciting bids for each species and size of seafood.

Located about 45 minutes south of Portland, the charming coastal village of Kennebunkport features several Federal- and Victorian-style homes built by wealthy merchants and sea captains in the 1700’s and 1800’s. Today it is regarded as one of the most expensive vacation areas in the Northeast (the Bush family has a home here). Visitors can explore the small district of art galleries, seafood restaurants and souvenir shops.

Portland, Maine Restaurants

According to the Maine Restaurant Association, Portland is home to more than 200 restaurants. Although many restaurants are within the downtown area, some good ones are located on the outskirts and are worth the trek. Seafood is a staple, with lobster being the star. Almost every restaurant features a “lobster roll,” which is basically fresh-picked meat from the lobster brushed with sweet butter and served on a toasted roll with mayonnaise. Other traditional dishes include whole lobster boiled or steamed under seaweed at a seaside lobster bake.

For a truly Portland seafood experience, head to the Portland Lobster Company, specializing in you-know-what — lobster. Big appetites can order the Downeast Feast, which includes lobster, steamers (Maine steamed clams), corn on the cob, coleslaw and baked potato or fries.

Situated in a converted car ferry on the Portland waterfront, Dimillo’s on the Water offers fresh seafood with an Italian flair. Choose from items like the lobster roll, fried Maine shrimp and the Maine crab club, plus a number of traditional Italian dishes such as chicken parmigiana. While you dine, you can watch the sights and sounds of Portland Harbor from the outside decks or enjoy the water views from every window in the dining room.

Serving American comfort food made from local ingredients, the Front Room offers classics such as the Reuben sandwich, slow-cooked barbecue brisket or biscuits and gravy. The cozy restaurant boasts warm woodwork and lots of windows overlooking the scenic Eastern Promenade.

Eat where the locals eat at Becky’s On Hobson’s Wharf. Here you’ll see a mix of waterfront workers sitting at the long counter, elbow-to-elbow with tourists in the know. This diner-style restaurant serves generous breakfasts made from local ingredients, such as their French toast cooked with fresh-baked Italian bread. And the vast lunch menu includes items ranging from the ubiquitous lobster roll to a peanut butter and jelly sandwich (or peanut butter and bacon!), along with typical diner fare such as all-day breakfasts and burgers.

Duckfat is a European-style fry and sandwich shop with reasonable prices. Their Belgian fries are cooked in duck fat for a unique flavor and served in a paper cone, and the milkshakes are made from locally produced ice cream.

For an exciting gastronomical experience, 555 offers a brunch menu that is far from just bacon and eggs. Try the “traitor’s eggs” — poached eggs served with lobster meat and a lemony hollandaise sauce. The Maine Restaurant Association named owner/chef Steve Corry the 2011 Chef of the Year.

Combine sophistication, a garden setting and artfully presented meals, and you have Eve’s at the Garden. Located in the Portland Harbor Hotel, the restaurant offers seating outside in the courtyard by the fountain or inside the contemporary dining room. Menu items include lobster ravioli with butternut squash and grilled quail with fig and honey.

In Casco Bay, the Inn on Peaks Island is owned by the Shipyard Brewery and its pub offers views of the Portland skyline. Choose from menu selections such as burgers, wraps or the signature Buffalo-fried Maine shrimp — beer-battered shrimp served with a blue cheese dip and a spicy Buffalo sauce.

On the rocky shores of Cape Elizabeth, adjacent to the famous Portland Head Light, sits the Lobster Shack at Two Lights. Enjoy the inexpensive yet fresh menu selections at picnic tables that overlook the surf, or eat inside the dining room, which features simple furnishings and large picture windows.

Shopping in Portland, Maine

The Old Port area is a fun place to browse clothing boutiques and specialty shops. If you’re looking for classic Portland souvenirs, seek out anything that celebrates Maine’s lobsters, lighthouses or maritime industry. Porte 4 sells fine jewelry with nautical designs such as 18K gold sailboat and lighthouse pendants. For unusual and historical nautical artifacts, check out China Sea Marine Trading Company.

Another unique souvenir is Sea Bags’ handmade water-resistant tote bag made in Maine from recycled sails. The company’s headquarters is located on Portland’s working waterfront at 25 Custom House Wharf.

Stepping in to fill the void left by the Portland Public Market, which folded in 2006, the Public Market House is the spot to indulge in local gourmet foods, fresh-baked bread and Maine-made beer.

Shopping die-hards won’t want to miss a trip to nearby Freeport. The well-known outlet shopping destination includes the L.L. Bean flagship store, which is open 24 hours a day and 365 days a year. Aside from merchandise, the store also has a 24-foot riverbed aquarium alive with fish and turtles native to Maine.

Looking for antiques? Check for listings of dealers in and around Portland.

–written by Renee Ruggero

We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

Top Fares From