15 Best Things To Do in Portland, Maine

If you're craving a coastal escape brimming with history, art, and lobster, pack your bags and set your GPS for Portland, Maine. The best things to do in Portland can keep you busy for days.

Get ready to stroll through the cobblestone streets of the Old Port District, where you'll find an eclectic mix of shops and eateries.

Morning walks along the Eastern Promenade Trail provide scenic views of Casco Bay, as does the historic Portland Observatory on a clear day.

But wait, there's more! From the vintage charm of the Maine Narrow Gauge Railroad to the architectural elegance of the West End and Victoria Mansion, Portland is a feast for the eyes.

Art lovers will appreciate the Portland Museum of Art, while literature buffs can step back in time at the Wadsworth-Longfellow House.

Foodies, we've got you covered, too. Embark on a walking food tour to sample the city's culinary delights, and don't miss out on a traditional lobster bake. It's Maine, after all!

And let's not forget the lighthouses. Whether it's the iconic Portland Head Light or the lesser-known Bug Light and Spring Point Ledge Lighthouse, these beacons offer picture-perfect backdrops.

So, whether you're an adventurer, a history nerd, or a food and art lover, Portland, Maine, has something for you.

Let's take a closer look at all of the fun things to do in Portland, the largest city in Maine.

Downtown Portland

1. Old Port District and Waterfront

The Old Port District in Portland, Maine, is steeped in history, offering a glimpse into the city's storied past.

Originally a bustling seaport in the 19th century, the area was the economic engine of Portland, facilitating trade and fishing.

The district's historic significance is evident in its well-preserved architecture, featuring red-brick facades along cobblestone streets.

However, the Old Port hasn't always been the trendy hotspot it is today. It declined during the mid-20th century, with many of its historic buildings facing demolition.

Thankfully, revitalization efforts in the '70s breathed new life into the district.

Today, those same buildings house clothing boutiques, art galleries, and some of Portland's best restaurants, including Central Provisions and Fore Street Restaurant.

The two-block pedestrian alleyway known as Wharf Street is lined with bars, bringing young people to the Old Port on the weekends to drink and party.

Commercial Street forms the eastern border of the Old Port District. Across the street, the Waterfront is lined with piers and wharves, some of which boast restaurants.

Here, you can depart on picturesque boat tours or catch the ferry from the Maine State Pier to Casco Bay islands.

The Old Port and Waterfront districts are a testament to Portland's resilience and continual evolution.

2. Portland Observatory

If you want a unique experience in Portland, Maine, head for the Portland Observatory. This maritime signal tower, built in 1807, is the last of its kind in the United States.

It is 86 feet tall and offers panoramic views of Portland Harbor and the city skyline. But it's not just the views that make this spot special; it's the history.

Initially constructed by Captain Lemuel Moody to serve as a communication hub for incoming ships, the Observatory played a crucial role in Portland's maritime history.

A flag system signaled to merchants in the city, letting them know what goods were arriving.

Today, the Observatory is a National Historic Landmark with guided tours that delve into its fascinating past.

Whether you're a history buff or just in it for the views, visiting the Portland Observatory is one of the best things to do in the city.

Pro Tip: If possible, time your visit to the Observatory with the opening hours of Belleville, a great place to grab fresh pastries across the street.

3. Eastern Promenade Trail

The Eastern Promenade is a 68-acre public park designed in the late 19th century by the Olmsted Brothers, disciples of Frederick Law Olmsted (the genius behind Central Park).

It's a blend of natural beauty and historical significance. Overlooking Casco Bay, the “Eastern Prom,” as locals call it, served as a strategic point during World War II, with remnants of fortifications still visible.

The Eastern Promenade Trail, part of the East Coast Greenway, offers stunning ocean views for cycling, jogging, or a stroll.

The Eastern Prom Food Truck Park offers affordable dining options in a central parking lot. And the East End Beach is the perfect place to relax during the warmer months.

Another notable element is Fort Allen Park, on the grounds of a former Revolutionary Way Fort built in 1775.

The 10-acre park commemorates those who fought for the United States with multiple memorials:

• USS Portland Memorial
• USS Maine Memorial Cannon
• 9/11 Memorial
• Arctic Memorial

The Eastern Prom is also home to the historic Narrow Gauge Railroad, where you can hop on for a nostalgic ride along the waterfront.

From live music in the summer months to winter sledding, the Eastern Promenade is a year-round destination, embodying Portland's rich history and love for the great outdoors.

The Eastern Prom is easy to pair with a trip to the Portland Observatory. It's a five-block walk north along Congress Street.

4. Maine Narrow Gauge Railroad

This railroad is a throwback to the late 19th and early 20th centuries when narrow-gauge lines were essential to Maine's transportation network.

Initially, these smaller tracks (just two feet wide) were built to navigate the state's rugged terrain, connecting remote communities and industries like logging and mining to larger cities.

Today, the Maine Narrow Gauge Railroad Co. & Museum offers a unique experience that transports you back in time.

Operating along a 1.5-mile stretch beside Casco Bay, the railroad uses actual historic cars and locomotives, some dating back to the 1800s.

The museum adjacent to the railroad adds context, showcasing artifacts and sharing stories about the impact of these railroads on Maine's development.

While I didn't have time to ride on Maine's Narrow Gauge Railroad, it reminded me of when I took a ride on another, the Darjeeling Himalayan Railway in India.

5. West End

The West End in Portland, Maine, is a neighborhood that exudes wealth and elegance.

Developed primarily in the late 19th and early 20th centuries, the area is an architectural showcase from the Queen Anne to Italianate styles.

Once home to Portland's elite, including sea captains and business magnates, the West End has always had a touch of grandeur.

A great way to get a full appreciation for this part of Portland is to take the history and architecture walking tour by Maine Day Ventures.

You'll learn far more about the city and buildings in the company of a knowledgeable local guide.

Today, the West End remains one of Portland's most desirable neighborhoods. It's also home to the Western Promenade, a public park offering sunset views.

6. Victoria Mansion

The Victoria Mansion, also known as the Morse-Libby House, is one of the West End's most notable buildings.

Built between 1858 and 1860, this National Historic Landmark offers a glimpse into the opulent lifestyle of the period.

I highly recommend the guided tour to see the richly-appointed interior, undergoing a complete room-by-room restoration, its first since the estate was built.

7. Portland Museum of Art

The Portland Museum of Art (PMA) is located in the heart of the Portland Arts District.

The museum is the state's oldest and largest public art institution. Founded in 1882, the PMA boasts an impressive collection that spans three centuries of American, European, and contemporary art.

The museum's architecture is a work of art, blending the historic McLellan House and the modern Charles Shipman Payson Building.

There's also a lovely sculpture garden accessible (for free) from the sidewalk during the museum's opening hours.

Inside, you'll find over 18,000 artworks, including pieces by iconic artists like Winslow Homer, Andrew Wyeth, and Edgar Degas.

The Portland Museum of Art also hosts rotating exhibitions, so there's always something new to see.

8. Wadsworth-Longfellow House

This historic home is where Henry Wadsworth Longfellow, one of America's most celebrated poets, spent his formative years.

Constructed in 1785 by his grandfather, General Peleg Wadsworth, the house is “the oldest standing brick structure on the Portland peninsula.”

Walking through the home feels like stepping back in time, thanks to its well-preserved interiors and period-appropriate furnishings.

The house is filled with family heirlooms and artifacts, offering an intimate look into the poet's life and his family.

A tour of the house provides fascinating insights into Longfellow's works, many of which were inspired by his New England upbringing.

Operated by the Maine Historical Society, the Wadsworth-Longfellow House is more than just a museum; it's a piece of American literary history.

Whether you're a fan of Longfellow's poetry or love historical homes, this spot deserves a place on your Portland itinerary.

9. Walking Food Tour

The Old Port Culinary Walking Tour by Maine Day Ventures is a foodie's dream come true.

Kick off your 3-hour gastronomic adventure at Andy's Old Port Pub, where you'll sip on a Maine craft beer and munch on a fresh fish taco.

Sustainability is the name of the game here, with seafood sourced directly from the Gulf of Maine.

Next, head to Luke's Lobster on Portland Pier. Enjoy a cup of New England clam chowder and a refreshing iced tea, all while soaking in the waterfront views.

You're steps away from where they catch their lobsters—talk about fresh!

Related: Best Things To Do in Bar Harbor

The tour doesn't stop there. Make your way to Rigby Yard, an industrial-chic bar, for a Maine Brewing Co.'s Lunch IPA and a delectable lobster roll.

Finally, satisfy your sweet tooth at Dean's Sweets with hand-dipped chocolate truffles made from locally sourced ingredients.

Guided by entertaining local experts like Timothy Goldkin, you'll feast on delicious food and learn about the Old Port's history and culture.

Islands

10. Lobster Bake

If you're in Portland, Maine, and you've got “eat a whole lobster” on your bucket list, hop on a Lucky Catch cruise for a sunset lobster bake on Peaks Island.

Trust me, this is not just a meal; it's a full-on Maine experience you won't forget. The outdoor adventure starts when you board the St. Croix, a 40-foot Maine-built lobster boat, and sail across Casco Bay.

You'll pass several lighthouses, including Bug Light and Spring Point Ledge Lighthouse, and get a hands-on lesson about lobsters and lobster fishing.

Once you arrive at Peaks Island, you'll head to Island Lobster Company, run by a local lobstering family.

Here, you'll be treated to a traditional Maine lobster bake that includes not just the star of the show—lobster—but also New England clam chowder, clams, corn on the cob, and potatoes.

And if you're nervous about dismantling that lobster, don't worry; you'll get step-by-step instructions.

So, whether you're a seafood lover or a lobster newbie, this cruise and lobster bake combo is a must-do.

It's a delicious, educational, and downright fun way to immerse yourself in Maine's coastal culture during the summer season.

11. Fort Gorges

If you're looking for an adventure in Portland, add Fort Gorges to your list. Situated on Hog Island Ledge in Casco Bay, this Civil War-era fort is only accessible by boat.

Built in the 1860s, the fort was deemed obsolete by the time it was completed, thanks to advancements in artillery technology.

Once you arrive, you're free to explore the fort's labyrinthine passageways, dark chambers, and parapets, all while enjoying panoramic views of the bay and Portland's skyline.

Wear sturdy shoes and bring a flashlight—the fort is largely unrestored and can be uneven.

Whether you kayak there at low tide or take a guided boat tour, visiting Fort Gorges offers a unique perspective on Portland's maritime history.

Lighthouses

12. Portland Head Light

No trip to Maine would be complete without a visit to the iconic Portland Head Light, which dates back to 1791.

Situated in Fort Williams Park, this historic lighthouse is the oldest in Maine and one of the most photographed in the United States.

The lighthouse still functions today, guiding ships safely through the entrance of Portland Harbor. But it's not just the lighthouse that draws visitors; the surrounding park offers activities, too.

Explore the cliffside walking trails for views of the Atlantic Ocean, check out the remnants of Fort Williams, or have a picnic while watching the sailboats.

The on-site museum, located in the former Keeper's Quarters, provides fascinating insights into the lighthouse's history and the lives of its keepers.

13. Cape Elizabeth Light East Tower

A short drive south of Portland Head Light is the Cape Elizabeth Light East Tower, another must-see lighthouse.

Also known as Two Lights, this lighthouse is one of a pair, though only the East Tower is active today.

Perched on dramatic cliffs, the lighthouse provides a perfect backdrop for photos.

While the tower is not open to the public, you can explore the surrounding area, which offers panoramic views of the Atlantic Ocean.

Don't forget to visit the nearby Two Lights State Park for hiking or a seaside picnic. At 41 acres, it's a small, serene spot encapsulating Maine's coastal appeal.

14. Bug Light

For a lighthouse experience that's a bit off the beaten path, check out Bug Light in South Portland.

Officially known as the Portland Breakwater Lighthouse, this charming structure is petite but packs a punch in terms of history and beauty.

Built in 1875, its design was inspired by an ancient Greek monument, giving it a unique, ornate look.

The park surrounding Bug Light is perfect for picnics, kite flying, or simply soaking in the views of Portland Harbor and the city skyline. It's also a popular spot for fishing and boating.

15. Spring Point Ledge Lighthouse

This caisson-style lighthouse in South Portland has guided vessels since 1897.

One of Spring Point Ledge Lighthouse's unique features is the 900-foot granite breakwater that connects it to the mainland, offering visitors a rare chance to walk right up to a lighthouse.

The journey along the breakwater is an adventure, providing terrific views of Casco Bay and the Portland Harbor.

Conclusion

Portland, Maine, is a treasure trove of experiences, blending maritime history, culinary innovation, and natural beauty into a destination that captivates every traveler.

From the cobblestone charm of the Old Port District to the picturesque lighthouses that dot its coastline, Portland offers a plethora of fun things to see and do.

Whether you're a foodie eager to dive into a traditional lobster bake, a history buff fascinated by forts and observatories, or an art lover drawn to the city's galleries and museums, you'll find something to love in this coastal community.

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This story is based on my experiences during two trips to Portland, Maine. The first visit was as a media attendee of the ATTA AdventureELEVATE North America conference at the Holiday Inn Portland by the Bay. Accommodation at Aloft Portland was provided in collaboration with Visit Portland during my second visit. I received complimentary food and architecture tours courtesy of Maine Day Ventures.