Top Portland Outdoor Activities

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation or renting a car on this small-group guided tour of Portland's must-see sights. Stop in downtown Portland and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Learn about Portland's history with this walking tour, which will take you through the Old Port, downtown, and waterfront areas. You'll see all sorts of historic attractions, including the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church, all with a professional guide on hand to share stories about the city's past.

The streets of Portland, Maine, are the site of this exciting scavenger hunt. Scour these city streets in search of a variety of objects, landmarks, and works of art. You’ll be given clues about the town’s art, history, and culture to help you find your way from item to item. As you find and photograph each item, your team will earn points. Try to get the most points to rank highest on a leaderboard with other teams across the country completing other scavenger hunts.

Spend three hours kayaking through Casco Bay with this small-group tour led by a professional guide. You'll launch from Mere Point in Brunswick and paddle over to a couple of different islands, with the opportunity to see all sorts of marine birds, and maybe even a seal or two, along the way.

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.

Skip the generic, slow-moving walking tours—instead, explore Portland with your crew via scavenger hunt. Solve riddles, take wild photos, and complete challenges as your smartphone leads you across the city’s best landmarks, clue by clue. As you race the clock, learn all about Portland’s nooks and crannies, testing your mettle and your will to win.

Walk around Portland while completing the 3Quest Challenge scavenger hunt! Use our app to find a list of objects (provided in riddle form) around the city and participate in fun challenges for points. Collect points and take a look at your score compared to others on the app's leaderboard. All of the objects and challenges will be divided into 3 quests. Complete the 1st quest, 2nd quest, and 3rd quest, in order, to complete the game! Set a time limit of 2 hours for yourself if you'd like to make the challenge even more intense! During the game, you'll have a remote host who will follow along virtually with you and chat if you need any help! Come explore Portland with us by completing all 3 Quests!

Use an app to survive a zombie apocalypse in Portland . In Zombie Scavengers, explore the city however you'd like to search for items needed to survive a zombie apocalypse. You'll get points for finding these items. You can also do some zombie themed challenges for points on the app as well. Strategize in order to get the most points and survive the apocalypse. Your remote host will be there for you via chat if you need anything. Can you survive the apocalypse in Portland?

While walking tours are helpful for getting oriented, they rely on guides and discourage independent exploration. With this interactive scavenger hunt, explore Portland at your own pace while completing game-like challenges and hunting for particular items along the way. Submit photos of items found around the city, communicate with a game host via chat during the hunt, and compare scores with other teams across the country when you’re done.

During Crazy Dash of Portland, you'll use an app and walk through the city to collect points by finding items around the city and performing challenges. You can find the items in any order you want. Check out the rankings in the app to see your score compared to other teams across the nation. Crazy Dash comes with a remote host to chat with you in case you need anything. Crazy Dash is our most relaxed scavenger hunt. Come explore with us in Portland!

Holly Jolly Hunt is a scavenger hunt that is played using an app on your smartphone, that brings your entire family and friends together for holiday cheer. During the adventure you’ll be seeking out all the traditional, and even the non-traditional holiday items we all see this time of year around the city. You’ll get points for each item you find. The goal is to capture as many items as you can in order to score as many points as possible and get 1st place on the leaderboard. Along the way you’ll be asked to perform silly holiday themed tasks meant to bring laughter and smiles to everyone involved. Come play with us. Young or old, this is a scavenger hunt for everyone that enjoys this time of year. We promise you will create holiday memories that you will not forget! Holly Jolly Hunt can be played in any city!

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

Lighthouses are an iconic image associated with coastal Maine and Portland showcases some from the 1800s. Join this bicycling tour in Portland and see two of the city’s lighthouses from the 19th century. Follow quiet roads along South Portland’s coast to reach a small lighthouse called Bug Light, still in use today. Ride farther to Spring Point where a larger lighthouse awaits at the end of a long granite breakwater.

Experience the enchanting history of Portland through a captivating exploration! Solve intricate riddles and uncover local gems while learning fascinating trivia about the city's roots. This adventure encourages playful engagement—snap pictures of landmarks, answer questions about your surroundings, and embrace the unexpected (like pretending to fly!). It's the ultimate way to enjoy Portland's unique charm, discover its ties to Japan and the sea, and test your wits.

Step into the shoes of a newly-minted detective, tasked by Commander Mahoney to solve a gripping case. murder on the streets of Portland. Throughout this crime-solving audio adventure, visit each of the 10 mapped locations. You'll have the option to explore the downtown area using the Walking Map or follow a Driving Map on the city's outskirts. Refer to ‘Meeting Point’ for the starting location. See images for route. Park or stop at each location, listen to the audio story, and put your detective skills to the test by gathering clues and piecing together the evidence. Finally, make your deductions and issue an arrest warrant. Your overall detective skills will be evaluated, culminating in a Case Performance Score to measure your sleuthing prowess. This game is suitable for solo detectives, dynamic duos, or groups of mystery enthusiasts, offering an immersive audio tale filled with intrigue.

Set sail for some incredible sights off the coast of Portland, Maine. Keep your eyes peeled for local wildlife, and feel free to pick your captain and crew’s brains on the scenery. Kick back, relax, and bring your own snacks and drinks to enjoy as your captain sails towards wonderful views of lighthouses and historic forts.

Experience the beauty of Casco Bay and set sail from Portland, Maine for an unforgettable sunset cruise. Bring your own snacks and drinks, kick back, and relax as your captain sails towards incredible views. Feel free to ask your captain and crew questions about the scenery, and remember to keep your eyes peeled for seals and seabirds.

Join us for 1 1/2 hours as we cruise along the rugged coastline, complete with lighthouses, seals, seabirds, and historic forts. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the tranquil waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, cruising aboard Ruth is a unique adventure, a 39’ long classic, picnic style tour boat built in 1935 at Handy Boat in Falmouth, Maine.