Best Things to Do in Portland, Maine: 12 Must-Visit Attractions

by Jen
Best Things to Do in Portland, Maine
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Are you planning a trip to the East Coast? If so, you should definitely consider Portland, Maine. Here are some of the most unique, scenic, and fun-filled attractions in Portland, Maine. This coastal gem is known for its vibrant food scene, historic charm, and breathtaking landscapes, making it a must-visit destination for any New England itinerary.

Portland, Maine, is a city that beautifully blends the old with the new. Its historic waterfront, the Old Port, is filled with quaint cobblestone streets, 19th-century brick buildings, and fishing piers. As such, they give you a glimpse into the city’s rich maritime past. Portland is also a city that embraces the present and looks forward to the future, with its thriving arts scene, innovative craft breweries, and sustainable farm-to-table restaurants. As such, there is no shortage of places to visit and things to do in Portland, Maine.

From the iconic Portland Head Light to the bustling Portland Public Market, there are countless activities for every kind of traveler. That’s why it’s important for you to know which places are best suited for your particular interests. To help, I’ve compiled a list of some of my personal favorite Portland attractions. Check it out! Here’s everything you need to know about these fun things to do in Portland, Maine.

The top places to visit in Portland, Maine right now
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Best Places to Visit in Portland, Maine

Ready for a journey through all the coolest things to do in Portland, Maine? As noted above, there’s something for everyone at this remarkable vacation destination. So read on to discover all these unique Portland, Maine places to visit.

Are you into exploring city attractions and historical sites? Or would you prefer a tranquil getaway in nature? Whatever you’re planning, these must-sees in Portland, Maine can accommodate your needs. Here’s all the best attractions in Portland, Maine that you should know about.

1. Old Port

This is one of the best things to do in Portland, Maine, hands down. The heart of Portland, Maine, Old Port is a vibrant district that beautifully marries the past and the present. As you wander through the cobblestone streets, you’ll be transported back in time, with the 18th and 19th-century buildings now housing a variety of trendy boutiques, cafes, and bars. The key to exploring Old Port is to familiarize yourself with its main streets. Commercial Street, right next to the water, is home to mid-1850s Greek Revival warehouse buildings. Wharf Street, the original edge of Old Port’s harbor, still boasts authentic cobblestones from its ship ballast days.

Venture along Silver Street or Market Street until you reach Middle Street. This is where the meeting areas have been designated a National Historic District. The Victorian Commercial architecture lining both sides of Middle Street is a sight to behold. Don’t miss out on Congress Street, home to Henry Wadsworth Longfellow’s boyhood home, now a museum. There are also several parks around this area, such as Post Office Park and Tommy’s Park. Finally, make your way to Exchange Street, the hub of action, brimming with boutique shops, cute cafes, bookstores, art stores, and historic architecture.

The Old Port is undoubtedly one of the best places in Portland, Maine to soak in the city’s rich history while enjoying modern amenities. It’s easy to see why a stop here is one of the best things to do in Portland, Maine.

Old Port is a charming district blending history and modernity through cobblestone streets, trendy shops, cafes, and historic buildings.
Old Port is a charming district blending history and modernity through cobblestone streets, trendy shops, cafes, and historic buildings.

2. Peaks Island

For an experience like no other, you’ll want to check out this top place to visit in Portland, Maine. Just a short ferry ride from the mainland, Peaks Island is a hidden gem that offers a delightful escape from the hustle and bustle of downtown Portland. This charming island, nestled in the heart of Casco Bay, is a haven for outdoor enthusiasts and those seeking a tranquil retreat.

With its laid-back vibe and picturesque landscapes, Peaks Island is a favorite among locals and tourists alike. The island’s winding roads and trails invite you to explore its natural beauty. You can rent a bike or a golf cart and set off on an adventure, discovering hidden beaches, historic sites, and stunning ocean views.

Don’t forget to check out the local shops and galleries, where you can find unique souvenirs and artworks. The island is also home to a vibrant community of artists, adding a touch of culture to your visit.

After a day of exploration, you can enjoy a delicious meal at one of the island’s restaurants, offering fresh seafood and local delicacies. Visiting Peaks Island is undoubtedly one of the coolest things to do in Portland, Maine, offering a unique blend of tranquility, adventure, and cultural experiences. It’s a must-see destination that should be on every traveler’s itinerary.

3. Portland Museum of Art

Experience New England in style at this unique place to visit in Portland, Maine. For those who appreciate the finer things in life, the Portland Museum of Art is a must-visit destination in Portland, Maine. This cultural gem, founded in 1882, is one of the oldest and largest public art institutions in the state, housing an impressive collection of over 22,000 artworks.

The museum’s collections span a wide range of periods and styles, from European and American art to contemporary works. It’s a place where you can admire the brushstrokes of world-renowned artists like Claude Monet and Winslow Homer, and also discover the creative genius of Maine’s local artists. The museum’s extensive collection includes paintings, sculptures, prints, photographs, and decorative arts, ensuring there’s something to pique the interest of every art enthusiast.

In addition to its permanent collection, the museum hosts rotating exhibitions and a variety of educational programs and events throughout the year. These programs provide visitors with a deeper understanding of the art and artists, making the museum a hub of cultural activity and learning.

So, if you’re compiling a list of the best things to do in Portland, Maine, make sure a stop at the Portland Museum of Art is at the top. It’s a journey through the world of art that will leave you inspired and enriched.

Just a ferry ride away, Peaks Island—a tranquil haven in Casco Bay, perfect for outdoor enthusiasts and relaxation seekers.
Just a ferry ride away, Peaks Island—a tranquil haven in Casco Bay, perfect for outdoor enthusiasts and relaxation seekers.

4. Eastern Promenade

One of the most cherished places in Portland, Maine to visit is the Eastern Promenade. This 68-acre park is a sanctuary of tranquility, offering a picturesque waterfront view that is sure to captivate your senses. Visiting the Eastern Promenade is one of the most fun things to do in Portland, Maine, with its extensive network of hiking and walking trails, sports courts, playgrounds, and serene grassy areas perfect for a leisurely picnic.

The Eastern Promenade Trail, which was once an old railway line, is a must-see in Portland, Maine. It takes you through the heart of the park, leading you to Fort Allen Park and its beautiful shoreline. From there, you can climb a grassy hill for an unbeatable view of the city and harbor.

Just a short walk away is East End Beach, where you can indulge in a refreshing swim or simply bask in the sun. The Eastern Promenade is more than just a park; it’s a testament to Portland’s commitment to preserving its natural beauty. It’s a place where you can escape the hustle and bustle of the city, breathe in the fresh air, and immerse yourself in the calming rhythm of nature.

So, if you’re wondering what to do in Portland, Maine, a visit to the Eastern Promenade should definitely be on your list. It’s a place where you can relax, rejuvenate, and reconnect with nature, all while enjoying the stunning views of the city and the harbor. It’s truly one of the best places to go in Portland, Maine.

Visiting Eastern Promenade is one of the best things to do in Portland, Maine.
Eastern Promenade—a 68-acre waterfront park with hiking trails, sports courts, playgrounds, and serene picnic spots for a delightful visit.

5. International Cryptozoology Museum

Yearning for a getaway like no other? This thing to do in Portland, Maine has got you covered. The International Cryptozoology Museum is a treasure trove of fascinating and somewhat eerie displays of creatures that may or may not exist. From the infamous Loch Ness Monster to the elusive Bigfoot, the museum is a testament to the human fascination with the unknown and unexplored.

The museum is located in the heart of Portland’s Arts District, a vibrant neighborhood known for its high concentration of galleries, museums, and performing arts venues. It’s a great place to immerse yourself in the city’s creative side and explore the intriguing world of cryptozoology.

The museum’s collection is vast and varied, featuring exhibits that will pique the curiosity of both young and old visitors. It’s a place where imagination meets science, and where the line between reality and myth is blurred. A skeptic or a believer? The International Cryptozoology Museum offers a unique and engaging experience that you won’t find anywhere else.

Try one of the coolest things to do in Portland, Maine, with a visit to the International Cryptozoology Museum. You’ll be able to delve into the world of cryptids and discover the mysteries that lie beyond the realm of known biology. It’s an adventure that promises to be as enlightening as it is entertaining.

International Cryptozoology Museum: explore eerie creature displays and indulge in the fascination of the unknown.
International Cryptozoology Museum: explore eerie creature displays and indulge in the fascination of the unknown.

6. Portland Observatory

Looking for a bird’s-eye view of Portland? Then the Portland Observatory is one of the coolest places to visit in Portland, Maine. This 86-foot-high octagonal tower, built in 1807, is the last remaining maritime signal tower in the United States. Located on Congress Street near Old Port, the observatory is open to the public from late May to early October.

Join a guided observatory tour, which lasts 45 minutes and gives you access to the top of the tower via a set of long, winding stairs. There’s no elevator going up, so it’s a bit of a workout, but the views of Portland from the top are truly unforgettable!

The Portland Observatory is truly a unique place in Portland, Maine. It’s a testament to the city’s rich maritime history. As you climb the stairs and reach the top, you’ll be rewarded with panoramic views of the city and harbor, making it one of the coolest Portland, Maine things to do.

The Portland Observatory is a must-visit in Portland, Maine. So, next time you’re wondering where to go in Portland, Maine, make sure the observatory is on your list.

Remember, the journey to the top might be a bit of a workout, but the breathtaking views of Portland are worth every step. After all, there’s nothing like seeing a city from above to truly appreciate its beauty and charm. So, lace up your walking shoes and get ready for an unforgettable experience at the Portland Observatory. As such, I recommend this thing to do in Portland, Maine to everyone I meet.

Portland Observatory—an 86-foot maritime signal tower offering unique views. Open late May to early October near Old Port.
Portland Observatory—an 86-foot maritime signal tower offering unique views. Open late May to early October near Old Port.

7. Munjoy Hill

As far as things to do in Portland, Maine go, this activity is among the coolest! Munjoy Hill, with its most vibrant neighborhoods, is a must-visit in Portland, Maine especially for anyone seeking a blend of history, culture, and gastronomy. This neighborhood, which dates back to the 1630s, is now a trendy hotspot known for its stunning hilltop views of the city, bustling parks, and fantastic restaurants and cafes.

Start your day with a cup of coffee at the local favorite, Hilltop Coffee Shop, and then head over to The Front Room for a delightful brunch. After fueling up, visit the Maine Narrow Gauge Railroad Co. and Museum, which offers rides on vintage trains as part of its mission to preserve Maine’s railroading heritage.

End your day in Munjoy Hill by dining at one of the neighborhood’s eateries. The food scene here is a foodie’s dream come true, with a variety of options to choose from. In the mood for seafood, Italian, or a good old-fashioned burger? Munjoy Hill has got you covered.

So, if you’re wondering where to go in Portland, Maine, Munjoy Hill should be on your list. Its unique blend of history, culture, and culinary delights make it a must-visit destination in Portland. As one of the top Portland, Maine attractions, you’ll definitely want to add this to your travel itinerary.

Munjoy Hill is one of the best things to do in Portland, Maine.
Munjoy Hill is a historic neighborhood with hilltop views, parks, and fantastic dining, blending culture, history, and gastronomy.

8. The Maine Narrow Gauge Railroad Co. & Museum

Are you looking to discover history at its finest? The Maine Narrow Gauge Railroad Co. & Museum is one of the coolest things to do in Portland, Maine. This unique museum is dedicated to preserving the state’s railroading heritage, offering visitors a chance to step back in time and experience the charm of vintage trains.

Located near the trendy neighborhood of Munjoy Hill, the museum is home to a collection of narrow gauge railway equipment used in Maine during the late 19th and early 20th centuries. The highlight of your visit will undoubtedly be the chance to ride on one of these historic trains. The scenic ride along the Eastern Promenade of Casco Bay offers stunning views of the waterfront and is a hit with both kids and adults.

The museum offers educational exhibits that provide insights into the history and significance of narrow gauge railroads in Maine’s industrial past. You’ll learn about the people who built and operated these railroads, and the communities that depended on them.

After your visit, why not explore the rest of Munjoy Hill? This vibrant area is known for its eclectic entertainment spots, great restaurants, and cafes. It’s the perfect place to grab a bite or a coffee after your museum adventure.

So, if you’re wondering where to go in Portland, Maine, make sure to add the Maine Narrow Gauge Railroad Co. & Museum to your itinerary. It’s a fun and educational experience that’s sure to leave you with lasting memories of your visit to Portland.

Maine Narrow Gauge Railroad Co. & Museum—a unique destination preserving the state's railroading heritage with vintage trains.
Maine Narrow Gauge Railroad Co. & Museum—a unique destination preserving the state’s railroading heritage with vintage trains.

9. Arts District

Looking for the best things to do in Portland, Maine? Don’t miss this one! Portland is a vibrant hub for the arts, and nowhere is this more evident than in the city’s Arts District. This area is home to a high concentration of galleries, museums, and performing arts venues, making it a must-visit in Portland, Maine for any art enthusiast.

Start your exploration at the Children’s Museum & Theatre of Maine. This massive 30,000 square foot space is packed with interactive exhibits that will delight both kids and adults. From a mini bank and shipyard to a market and even a pirate boat, there’s plenty to keep the whole family entertained.

For a taste of local history, head to the Maine Historical Society. This institution traces Maine’s roots from the time of the European settlers to the present day. You can also visit the Wadsworth-Longfellow House, the childhood home of one of America’s first poets.

The Arts District is a testament to Portland’s creative spirit. It’s a place where you can immerse yourself in the city’s rich cultural tapestry and discover the unique places in Portland, Maine, that make it so special. Make sure to add the Arts District to your Portland itinerary.

The vibrant Arts District boasts galleries, museums, and performing arts venues—a haven for art enthusiasts visiting the city.
The vibrant Arts District boasts galleries, museums, and performing arts venues—a haven for art enthusiasts visiting the city.

10. Victoria Mansion

One of the coolest Portland, Maine things to do is to step back in time and visit the Victoria Mansion. This historic house museum, built between 1858 and 1860, is often considered one of the best-preserved examples of pre-Civil War architecture in the United States. The Italianate style of the mansion is evident in its mansard roof, ironwork balcony, and decorative cornices.

Inside, the mansion is just as stunning, with hand-painted murals, imported marble fireplaces, and intricately carved woodwork. Ninety percent of the original furnishings are still on display, making it easy to imagine what life was like for the original occupants of the mansion.

You can visit Victoria Mansion from May 1 to October 31 every year, during which it’s open seven days a week. It’s located in Downtown Portland, a half-mile south of Old Port, so you can easily add it to your Portland itinerary if you’re spending a day exploring the area.

Visiting the Victoria Mansion is like stepping into a time capsule, offering a glimpse into the opulence and grandeur of a bygone era. It’s a must-see in Portland, Maine, for history lovers and architecture enthusiasts alike.

Victoria Mansion is one of the best things to do in Portland, Maine.
Step back in time at this well-preserved 1858 Italianate mansion, showcasing pre-Civil War architecture with distinctive features.

11. Palace Playland

Looking to visit one of the best places in Portland, Maine? Add this to your bucket list! Located a few miles south of Portland in Old Orchard Beach, Palace Playland is one of the unique places in Portland, Maine known as “Maine’s only beachfront amusement park.” The park’s rides directly overlook the water, offering an exhilarating experience with stunning ocean views.

Palace Playland offers a variety of entertainment options. From games, slides, carousels, bumper cars, kiddie pools to fun houses, there’s something for everyone. The park also houses an arcade filled with photobooths and skeeball lanes, and numerous snack stalls to keep your hunger at bay.

What sets Palace Playland apart is its location. The amusement park is situated such that when you’re screaming on the roller coaster or relaxing on the Ferris wheel, you’re doing it with incredible ocean views. This unique feature makes it one of the must-visit attractions in Portland.

You could spend an entire weekend at Palace Playland with all of its games and amusements. And the view from the top of its gigantic rides is something you won’t get anywhere else. So, if you’re looking for the most fun things to do in Portland, Maine, consider Palace Playland. It’s an experience you won’t forget!

Palace Playland in Old Orchard Beach. Maine's sole beachfront amusement park offers thrilling rides and ocean views.
Palace Playland in Old Orchard Beach. Maine’s sole beachfront amusement park offers thrilling rides and ocean views.

12. Rockin’ Horse Stables

It would be a crime to write an article on the top things to do in Portland, Maine without mentioning the Rockin’ Horse Stables in Kennebunkport. For a truly unique experience, head to the Rockin’ Horse Stables. It’s  just a short drive from Portland. This charming establishment offers a variety of horse-drawn rides. This includes carriage rides and sleigh rides, making it one of the most romantic Portland things to do.

Winter is the best time to visit the Rockin’ Horse Stables. With fresh snow blanketing the ground, you can cuddle close under a cozy blanket while enjoying a sleigh ride for two. You’ll also be treated to complimentary hot chocolate when you return to the stables! Romance can bloom in spring and summer, too. A horse-drawn carriage ride can seem like something out of a storybook as you explore the lush green countryside.

For an extra-magical experience, you can arrange for the driver to take you to a quaint little bed-and-breakfast at the end of your trip. Visit the Rockin’ Horse Stables if you’re hoping to have a fanciful time in Portland. With so much charm and personality, the Rockin’ Horse Stables is one of the top places to visit in Portland, Maine.

Experience romantic horse-drawn carriage and sleigh rides just a short drive away at Rockin’ Horse Stables.
Experience romantic horse-drawn carriage and sleigh rides just a short drive away at Rockin’ Horse Stables.

Frequently Asked Questions (FAQs) about the Best Things to Do in Portland, Maine

Looking for more content on the top things to do in Portland, Maine? Here are some popular questions (and answers) I get that will help you plan your trip to Portland:

When is the best time to visit Portland, Maine?

Portland, Maine, is a year-round destination, but the best time to visit depends on what you want to do. For outdoor activities and festivals, summer and fall are the best seasons. Winter, on the other hand, offers unique experiences like ice skating and winter festivals.

Is Portland Maine worth visiting?

Yes, Portland, Maine, is indeed worth visiting, and it has much to offer to travelers. As the largest city in Maine, Portland is known for its vibrant arts scene, historic architecture, and stunning waterfront.

The Old Port district is a must-see, with its cobblestone streets, 19th-century brick buildings, and an array of boutiques, galleries, and restaurants. Here, you can enjoy some of the freshest seafood, including the famous Maine lobster. The city’s culinary scene is renowned, offering everything from gourmet dining to food trucks, all showcasing local ingredients.

Portland’s proximity to the sea means there are plenty of opportunities for sailing, fishing, and enjoying the beautiful coastal views. The city is also home to several lighthouses. This includes the iconic Portland Head Light, which is a popular spot for photography.

For art enthusiasts, the Portland Museum of Art houses an impressive collection of American, European, and contemporary art. Outdoor lovers will appreciate the nearby parks and trails, such as the Eastern Promenade, offering scenic views of Casco Bay.

With its blend of cultural attractions, natural beauty, and culinary delights, Portland, Maine, provides a unique and enjoyable experience for various interests and tastes. Whether you’re a foodie, history buff, or nature lover, Portland has something special to offer.

What are the must-see attractions in Portland, Maine?

Portland, Maine, is known for its vibrant arts scene, historic lighthouses, and beautiful parks. Some must-see attractions include the Portland Head Light, the Old Port district, and the Eastern Promenade. For art lovers, the Portland Museum of Art is a must-visit.

Scenic view of Portland Head Lighthouse standing tall against a coastal backdrop.
Scenic view of Portland Head Lighthouse standing tall against a coastal backdrop.

What are the best outdoor activities in Portland, Maine?

Portland offers a wide range of outdoor activities. You can enjoy hiking and biking in the city’s parks, go sailing or fishing in Casco Bay, or take a scenic drive along the Maine coast. In winter, you can enjoy ice skating or cross-country skiing.

Is Portland, Maine a good tourist destination?

Absolutely! Portland, Maine is a fantastic tourist destination. It’s a city that effortlessly blends rustic New England charm with a vibrant arts scene and a foodie culture that’s recognized nationwide. Exploring the historic Old Port district, visiting the iconic lighthouses, or indulging in some of the freshest seafood? Portland offers a unique and memorable experience for all types of travelers.

What is Portland, Maine’s #1 attraction?

While it’s hard to pick just one, many would argue that the Portland Head Light is the number one attraction in Portland, Maine. This historic lighthouse, located in the stunning Fort Williams Park, is the oldest in Maine and offers breathtaking views of the rugged coastline. It’s a must-visit for any first-time visitor to Portland and a beloved symbol of the city’s maritime heritage.

Is there a lot to do in Portland?

Yes, there’s a lot to do in Portland, Maine, catering to a wide range of interests and preferences.

  1. Culinary Exploration: Portland’s food scene is renowned, and you can enjoy everything from gourmet meals to casual food trucks. Don’t miss the chance to try fresh seafood, especially the famous Maine lobster.
  2. Historic Sites: The Old Port district offers a glimpse into Portland’s history with its cobblestone streets and 19th-century architecture. Guided tours are available to learn more about the area’s rich past.
  3. Art and Culture: The Portland Museum of Art and other galleries showcase a variety of art collections. The city also hosts various cultural festivals and events throughout the year.
  4. Outdoor Activities: Enjoy the natural beauty of the area by visiting the Eastern Promenade or taking a ferry to the nearby Casco Bay Islands. Opportunities for hiking, biking, sailing, and fishing abound.
  5. Lighthouses: Portland is home to several iconic lighthouses, including Portland Head Light, offering great photo opportunities and beautiful coastal views.
  6. Shopping: From unique boutiques in the Old Port to larger shopping centers, Portland offers a variety of shopping experiences.
  7. Breweries: Portland has a thriving craft beer scene. Many breweries offer tours and tastings, making it a great destination for beer enthusiasts.
  8. Music and Nightlife: The city has a lively music scene with venues hosting live performances. They range from local bands to nationally recognized acts. There are also plenty of bars and clubs for those looking to enjoy the nightlife.
  9. Seasonal Activities: Depending on the time of year, you can enjoy seasonal activities like skiing or snowboarding in the winter. Or, you can take advantage of beach outings and outdoor festivals in the summer.

With its diverse offerings, Portland, Maine, ensures that visitors of all ages and interests can find enjoyable activities and attractions.

Final Thoughts on Exploring Portland, Maine

From its historic lighthouses to its vibrant arts scene, Portland, Maine, offers a unique blend of natural beauty and cultural richness. You’ll find plenty to see and do in this charming New England city. So why wait? Start planning your Portland adventure today and discover the unique places in Portland, Maine, that make it a must-visit destination on any New England itinerary.

For more travel inspiration, check out our other articles on New England destinations. For a weekend getaway or a longer vacation, we’ve got you covered with the best places to visit, things to do, and hidden gems to discover. Happy travels!

The top things to do in Portland, Maine for all types of travelers
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