Portland, Maine is a charming city found nestled in the picturesque New England region. While Portland is widely known for its fresh seafood and cobblestone streets, there are many experiences that make a trip worthwhile. Historic buildings, breath-taking scenery, and delicious food make it a go-to destination.
The coastal town of Portland, Maine has much to offer. Go back in time and tour a historic landmark such as the Wadsworth-Longfellow house. Or head to Portland’s notable harbor to get some fresh air and take a breezy stroll down the Eastern Promenade Trail. From boat tours to lobster rolls, there’s something here for everyone!
Whether you enjoy touring the many lighthouses that dot the coast, listening to live music during the longest happy hour, or fine dining in some of Portland's top restaurants, there is always something to do. Below we’ve included unforgettable experiences that are unique to Portland. Read on and discover what you should include on your next trip to this treasured city.
Outdoor Exploration Activities in Portland, Maine
1. Casco Bay Adventures
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Loved by locals, this is a must-do item. Casco Bay Adventures offer charter tours and water taxi services in South Portland.
They provide tours based on what you want to experience. Whether you are ready for an adventure or just want to cruise around the bay, they have tours to fit your needs.
Catch a glimpse of a few of Maine’s 60 lighthouses or learn how to fish for mackerel. You will also have a chance to see some wildlife such as seals, bald eagles, and porpoises. Whatever you’re interested in, they will customize and make your own “Maine Adventure.”
Their water taxi services are affordable and convenient for visiting the islands of Casco Bay. The rates vary based on where you are heading.
The rate for the taxi starts at $30 and goes up to $175. The captains are knowledgeable and experienced. This is a great way to expand your view of Portland.
2. Wicked Walking Tours
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Wicked Walking Tours is a unique experience that starts on 72 Commercial Street at Bell Buoy Park. It can be found between Flatbread and Casco Bay lines. This tour calls itself a Comedy of Haunted History, which is what makes it so unique.
Come visit, and you will see professional actors and comedians take some of Maine's dark history and turn it into theatrical year-round. It features creatures and entertainment like Ghosts, Witch Trials, Abenaki Attacks, Pirates, Storytelling, and standup.
This is one event that will have you coming back time and time again. If you want to be scared and laugh, come check it out!
Related Read: Best Time To Visit Maine
3. Cascade Falls Trail
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📍Map It: 951 Portland Rd, Saco, ME 04072 | Hours: Open daily and year-round. | Entrance: no fee
The Cascade Falls Trail is a short trail that is accessible for lots of people, including wheelchairs, the elderly, and children. This is due to its surface of stone dust. The trail is only about 0.3 miles long in total.
The Trout Pond Loop begins with a turn, either left or right. If you go left, you'll move through a pine and hardwood forest as the trail turns to the right along Cascade Brook.
Eventually, the trail moves toward an open area, where you can decide to turn back toward the trailhead or a steeper climb trail to the base of the falls. The site is unimproved and can be a bit more dangerous for some. There is a fantastic view of the falls, and on the other side of the brook, there is a trail to the top of the falls.
This beautiful and historic area has been popular since the late 1800s for fishing, picnicking, hiking, and of course, viewing the falls. Remember to keep your dogs on a leash, leave no trace, and pack plenty of bug spray.
4. Scarborough Beach State Park
📍Map It: Scarborough Beach State Park, 418 Black Point Rd, Scarborough, ME 04074 | Phone: (207) 883-2416 | Website | Hours: 9 am - 7 pm daily
Scarborough Beach State Park offers not only lovely views during different hours of the day but also a fun beach experience. There are also food trucks nearby, so if you get hungry, go stop at one of those to grab a bite to eat.
The price of a visit depends on where you are from. Maine residents pay between 8 to 16 dollars depending on age and whether they are surfing in the water. For non-residents, the prices range from 10 to 20 dollars depending on the same factors.
Bathrooms and showers are open for all visitors. There is also wi-fi available should you want to go on the internet at any point. The day pass is 7 dollars, and a four device 365 pass is 40 dollars.
Related Read: 20 Romantic Getaways in Maine
5. Portland Explorer Tours
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📍Map It: (Pick up location) Portland Beer Hub, 320 Fore St, Portland, ME 04101 | Phone: 207-835-4950 | Website | Entrance: Group Tours : $52, Seniors: $49, Children: $40; Private tours: $399 total for 10 passengers.
Portland Explorer Tours offers several different tours, such as their small group lighthouse tour, for only $52. You'll get a fully narrated, 2-hour tour of three scenic lighthouses for epic photo shoots, walking around the parks, and learning the history of the areas.
Since the company is family owned and local, the tour guides are incredibly knowledgeable about the area and history. For a private tour for up to ten people, you'll see three unique lighthouses.
You will also get to tour the working waterfront to see how the lobster industry works year-round. Along the tour through the City of Portland, you may see Commercial Street, the Working Waterfront, and Custom House Wharf.
More places on the list include the U.S. Custom Building, Casco Bay Lines, Casco Bay, Fore Street, Bug Light Lighthouse, the Portland Fish Exchange, and so much more!
Portland Explorer tours provide everything from brew and shopping tours to corporate and private tours. They share their love of Portland and its incredible history, as well as points of interest without making you feel like a tourist.
6. Bayside Bowl
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📍Map It: 58 Alder St. Portland, ME 04101 | Phone: 207-791-2695 | Website | Hours: Sunday - Thursday 4 pm – 10 pm, Friday & Saturday 4pm – 11pm | Entrance: $30/hr per lane Monday - Thursday, $35/hr per lane Friday - Sunday; Rooftop 21+ after 7 pm Friday and Saturday
Bayside Bowl is home to quite a few activities. Not only does it have twenty USBC sanctioned lanes of ten-pin bowling, but it also hosts several Pro Bowling League events. Whether an amateur or a pro, you can get your bowl on at Bayside Bowl.
Bowling leagues usually run Thursday through Sunday for all skill levels. You can reserve some lanes (if you give them 48 hours notice).
While you bowl, you can also use their fantastic "snack" bar, which has more than your usual nachos and fries. There are house-smoked wings, poutine, burgers, wraps, and salads. You can even grab a cocktail, wine, or craft beer to go with your nachos and wings.
Bayside Bowl also hosts parties and weddings. You could have your bachelor/ bachelorette parties, showers, and wedding all in one place!
Bayside does catering and has delicious cocktails from their full bar with an assortment of local craft beers. There are live music and events in the building, while on the rooftop, there are happy hour specials and free movie nights at sundown.
7. Eastern Promenade Trail
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This popular trail is used by locals to walk, bike, or run. The trail is two miles long and has unbeatable views of the harbor.
Take some time to view the local geography by taking a walk on this trail. You don’t need to complete it but be sure to make time for a short visit for scenic ocean views.
The trail is mostly flat, and it ends at Fort Allen Park. There are also benches and picnic tables available along the trail to take a quick rest or to stop and take in the views. It is a perfect place to plan a picnic lunch between sightseeing during the day.
8. Kettle Cove Beach
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📍Map It: Kettle Cove Rd, Cape Elizabeth, ME 04107 | Phone: (207) 799-5871 | Hours Open 24 hours daily
The Kettle Cove beach is next to the Crescent Beach State Park, so if you are visiting one, you might as well visit the other. Kettle Cove offers a lovely coastal view and a walking trail that goes around the cove.
This beach is great for just the view or if you want to swim and surf. Like with all bodies of water, make sure you are safe when swimming and monitor children. Other than swimming, you can ride a paddle, boat, or fish.
Really, the possibilities are endless and really just depend on your preference! If this sounds like something you want to do, consider giving Kettle Cove Beach a visit. Even pets are welcome, depending on the time of year!
Related Read: 11 Best Family Beaches in Maine
9. Rocky Bottom Fisheries
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📍Map It: 60 Portland Pier Street, Portland, ME 04101 | Phone: (207) 274-1844 | Website | Hours: 9 am - 7 pm Thursday through Tuesday, Hours 9 am – 7:15 pm Wednesday | Entrance: $50.00, adults, $35.00 ages 2-11, Children under 2 are free
Rocky Bottom Fisheries was created by a couple who grew up on and around the water. They now provide educational and fun tours for the public in Portland, Maine. The shining beacon has to be the Lobster Demonstration tours, where you get to trap lobsters and feel like a true Maine lobsterman.
The Casco Bay Sunset Cruise is a special offering for guests 21 and over. For those wanting a break from the kids or just to view the sunset, this cruise is for you. You can even add on a lobster roll from Luke's Lobster.
Private Charters are also available. This is great for those wanting to plan a birthday or graduation party, wedding, or corporate event, to name a few. It costs $325 for a minimum of two hours, so if you can afford it, book today!
10. Jewell Falls
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📍Map It: 167 Rowe Ave, Portland, ME 04102 | Phone: (207) 775-2411 | Hours: Open 24 hours daily
Jewell Falls sits on an 85-acre preserve and is the only natural waterfall that can be found in Portland. It is also the home to the Former Cumberland and Oxford Canal, which only adds to the history of this spot.
Think that is all there is to do here? Well, think again. Not only can you view the falls, you can also do some bird watching and or walk the trails.
This is also a popular area to engage in activities like mountain biking, snowshoeing, or cross-country skiing. If you bring your dog with you, then good news! They are allowed off-leash in this area, so as long as you monitor them, they are free to roam to their little heart's content.
Related Read: 20 Cabin & Treehouse Rentals in Maine
11. The Scenic Route Maine Tours
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Scenic Route Maine Tours was created by a couple, Khaled and Jen. They offer two main tours here. One is the City and Lighthouse tour, and the second is the Kennebunkport Tour.
The Lighthouse Tour is about two hours long and starts by showing you the Portland Observatory. After this, they show you Fort Allen Park, Longfellow Square, The Victoria Mansion, and the vibrant Arts District.
From there, you head to Fort Williams Park, which will offer many picture opportunities. In Kennebunkport town, you get a dose of town history and get to view the Wedding cake house and ocean vistas.
You will then have 90 minutes of free time before heading back. This tour lasts 3 hours and 30 minutes, so be sure to have your walking shoes ready!
12. Crescent Beach State Park
The Crescent Beach State Park has been open since 1966. It provides such activities as taking a dip in the ocean, a children's playground, a snack bar, and a bathhouse.
There also is the fact that this state park offers beautiful views of the ocean and a perfect opportunity for pictures! Its namesake is the mile-long, crescent-shaped beach. It is great for a multitude of activities that you can do by yourself or with family and friends.
During the off seasons, the park is closed to vehicles, but walkers are more than welcome to enjoy the beaches and trails. During winter, visitors can even hike or cross-country ski! No matter the season, there is always something to do at Crescent Beach State Park.
13. Love Locks
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The Love Locks is an interesting project that was created in Portland, Maine. Located around Commercial street, what you have is a 30-foot-long fence. This fence is then decorated with different variations of padlocks.
Basically, the padlocks symbolize everlasting affection. This is definitely a unique landmark in Portland, Maine.
It does not matter whether you plan to put a lock on it or simply view it. If you have a chance, consider giving it a visit. You certainly will not regret it!
Culture & Arts in Portland Maine
14. Portland Observatory
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📍Map It: 138 Congress St, Portland, ME 04101 | Phone: (207) 774-5561 | Hours: 10 am - 4 pm & 5 pm to 8 pm Thursday to Monday, Tuesday & Wednesday 5 pm to 8 pm
The Portland Observatory is a popular landmark in the city of Portland, Maine. It was first constructed in 1807 after Captain Lemel Moody ordered it to be constructed. This helped identify vessels as far as 30 miles away.
After the observatory fell into disrepair, it was restored and opened to visitors in 1939. By 1984, the Greater Portland Landmarks had taken over. Everything was going great until ten years later, serious moisture damage and infestation of power-post battles were discovered.
The tower was not opened until 2000 but had been growing ever since. It has been around for over 200 years now, so if you want to see a piece of Portland history, the Portland Observatory is the place to go.
15. Victoria Mansion
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Visit the Victoria Mansion and see the unique features and learn why it is one of the most important historic U.S. homes of the nineteenth century. There are guided tours offered at the mansion that last about 45 minutes. You may also tour at your own pace.
Also known as the Morse-Libby House, it has become a good example of the Italian Villa-style home in America. The mansion was built between 1858 and 1860. Almost all of the original wall paintings are in place, and much of the original décor has stayed intact.
The tour is designed for adults, but children are welcome to join in on tour. The mansion asks that if children come that they refrain from touching and climbing at this historic landmark.
16. Portland HeadLight
The Portland Headlight is a popular landmark that is owned and managed by the Town of Cape Elizabeth in Maine. Besides viewing the Lighthouse, there also is the Goddard Mansion, beach area, children's garden, Battery Blair & Keyes, and Ecology Project.
While you can view these 90+ acres yourself, you can also sign up for a tour in order to view all these sights. There is a $200 fee for tour buses entering the park. This is also charged per visit, so keep that in mind if you plan to go more than once.
Ultimately, it does not matter whether you take a tour or visit this place independently. The one thing that is for sure is that you will have an unforgettable experience visiting this magical destination.
17. Wadsworth-Longfellow House
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The Wadsworth-Longfellow house is the oldest standing building on the Portland peninsula. The house was originally built in 1786, and almost all the household items have been preserved and are still there today.
Come take a walk through history and learn about the contributions its founding family had to the community and New England. As the first wholly brick house in Portland, it is an important architectural history in Maine.
Tours are offered June-October. You can tour the house as well as take a look at the Longfellow garden on the property. Take a break from your trip in this peaceful Revival-style garden in the center of downtown.
18. Fort Gorges
📍Map It: Fort Gorges, Portland, ME 04101 | Phone: (207) 370-1181 | Hours: Monday through Saturday 6:30 am - 10 pm | Entrance: Guided Group tours: $63.60, Guided private tours: $318.00, otherwise free to the public
Fort Gorges is a former U.S. military fort built on Hog Island Ledge in the middle of Casco Bay. Begun in 1858 and finished in 1864, the fort did not see any military action, and no troops were stationed there. Due to advances in military technology, the fort was obsolete before it was needed or could be used.
The Fort is now a park, only accessible by boat, or kayak, as some visitors like to do. The fort is a D-shaped, two-story, enclosed fortress that has fallen into disrepair.
The Friends of Fort Gorges are attempting to maintain the building and the grounds, however. There are many rooms, nooks, and crannies to explore. Visitors should do so with care and knowledge that there are some dangerous areas.
19. Portland Museum of Art
Credit: Portland Art Museum / Flickr
The Portland Museum of Art is the largest and oldest public art museum in the state of Maine. It was founded in 1882 and had a versatile collection of pieces.
Included within the museum is also art created by Maine artists. Learn about Maine’s artistic history and some of its known artists.
Exhibitions are often hosted by the museum. These exhibitions highlight an artist with displays consisting of their special works. Check their Website to find out which artist will be highlighted on your visit.
There are also programs and events every month that are hosted by the museum. Take these into consideration when planning a visit.
Some programs include concert performances by Julliard graduate students. They also have films presented by local artists.
20. Running With Scissors Improv Comedy
Styled after Whose Line is it Anyway, Running with Scissors Improv has over 35 years of collective comedy experience. Performers often take suggestions from the audience.
Each set features the four founding members and sometimes guest actors. They are an 18 and over comedy troupe.
They are available for private parties, corporate events, and a night on the town. The performers can tailor their comedy for any group and audience. Some or all of the actors can be available to emcee your events as well.
For $300, Rachel Flehinger offers popular improv classes as well for those brave enough to face the journey. Students from her classes have gone on to do television shows, Broadway, movies, and more.
The classes aren't just for aspiring comedians, however. They are for anyone who wants to break out of their everyday routine and create something new and fun.
21. Portfiber Art Gallery
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The Portland Fiber Art Gallery and Weaving Studio was created before 2013 by Melodi Hackett. In September of that year, it was sold to employee Casey Ryder. While this business does have a new owner, it still is a place that supports the fiber arts community.
Not only can you purchase quality products here, but you can also join classes! They offer classes such as Spinning 101, a Fiber arts retreat, yarn party, and high spinning, to name a few.
New classes are always being announced, so always check the website for more info. Even if you are not much of an artist, it is still worth giving this place a visit!
Must-Try Food in Portland Maine
22. Luke's Lobster Portland Pier
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📍Map It: 60 Portland Pier, Portland, ME 04101 | Phone: 207-274-6097 | Website | Hours: Open Daily 11 am - 10 pm | Entrance: No fee, but only service dogs inside the restaurant. Dogs can be outside on the deck.
Luke's Lobster Shack is a consistent performer for locals and tourists alike! Not only has this seafood giant only been in business since 2009, but it is consistently winning awards and being featured for its fantastic food and its sustainability mission.
This year, Luke's was voted Best of Portland for Best View and Best Waterfront Dining. This is primarily since their flagship restaurant features 360° views directly off the edge of the pier, where you can watch the lobstermen bring in the daily catch to the lobster selling station.
The restaurant features its famous lobster rolls, seafood appetizers, steamed clams and mussels, lobster BLT, whole steamed lobster platter, fried or broiled haddock platter, and so much more! You can even order their lobsters and seafood to your house to cook yourself. Luke's even provides the recipes.
And, because Luke's knows the fishermen and processes the seafood at their facility in Maine, everything is as fresh as possible. Luke's buys directly from the fishermen's or fishermen's co-op to keep prices fair.
23. Portland Lobster Co.
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📍Map It: 180 Commercial St. Portland, ME 04101 | Phone: (207) 775-2112 | Website | Hours: Open Daily 11 am - 10 pm | Entrance: No fee, but only service dogs inside the restaurant. All leashed and well-behaved fur babies can be outside on the deck.
Another of Old Port's fantastic dining experiences, Portland Lobster Co. is an ideal location to enjoy one of the best lobster rolls in Portland. Their signature dish was voted the Best Lobster Roll of 2022, served by the Best Staff of 2022.
Portland Lobster Co.'s lobster roll is best described as sweet and buttery. The tail and claw meat are complemented by a touch of butter and a bed of romaine lettuce with mayonnaise and lemon on the side.
Portland Lobster Co. also invites guests onto the deck for daily live music to enjoy alongside their fantastic food, which goes beyond their excellent lobster roll. Their menu features clam chowder, lobster stew, crab and clam cakes, burgers and wraps, steamed lobster dinners, and fried seafood dinners.
Portland Lobster Co. also offers a fantastic view from their dockside deck and a tented outdoor bar overlooking Portland Harbor. Located in Old Port off the bustling Commercial Street, Portland Lobster Co. is ideally placed for those shopping and taking in the architecture and cobbled streets.
24. Harbor Fish Market
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Harbor Fish Market has been one of Portland's local landmarks in business since the 1800s. It is still one of the best places to score the freshest fish, shellfish, and lobsters.
You can set up your raw bar with a ton of oyster options, grill some swordfish, or take home sushi-grade tuna. Or you might find some rarer things, like shad roe, dorado, Maine shrimp, soft-shell crabs, and even more.
The staff knows their stuff, and they love helping you plan your next meal, often giving you recipes. You can even find tips on their Facebook page.
Just behind the counter is their processing room. There you can watch the workers cut, slice, and process the beautiful fresh fish, lobsters, and seafood.
Since the market is right on the Harbor, their lobsters come right off the lobster boats. They are brought through their back door and into aerated tanks. Each contains recirculating seawater for the freshest and best tasting seafood.
Because Harbor Fish Market is a working fish market, many of Portland's restaurants come to find rare species, specialty cuts, and the freshest seafood in Portland. Harbor Fish Market will also ship directly to your home, including live lobsters packed lovingly by real, actual people.
25. The Highroller Lobster Co.
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Maine is known for their lobster. The Highroller Lobster Co. is a great place to get a taste of their famous lobster. Since opening in 2015, it has become a popular place to eat for both locals and visitors.
The menu includes classics like the lobster roll and lobster grilled cheese. There are also more adventurous options like the lobster cheese crisp taco or the lobster corndog.
If you become a high roller fan, check out the merch shop online and show your support for this hometown favorite. Keep an eye out outside of Portland as they also like to go on the road and sell their famous food at breweries and beer fests all over the world.
26. Grippy Tannins Wine Tasting
Credit: Grippy Tannins / Yelp
At Grippy Tannins Wine Tasting, you get to taste a bunch of different wines that each have their own unique flavor. You can go to the tasting lounge or purchase it on the go. It really depends on your preference.
For in-store tastings, there is a rotating list of wines available by the glass and ½ glass. There are also cheese plates and charcuterie boards available should you want to enhance your visit a little. I mean, who doesn't love cheese and wine?
If you are in groups of 4 or more, you can reserve a customized tasting, which you will be brought to via plate!
This is done by the shop owner Lindsey Murray who will guide you through all the different wines. It can't get much fancier than that!
27. Browne Trading Market
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Browne Trading Market was created in 1991 and has been serving up some great quality and fresh seafood to Portland ever since. Purchase such delights as fileted fish, gourmet foods, artisanal cheese, specialty seafood, and caviar. They even have curated wine available to purchase!
Order online or in person. The choice is truly up to you. If you feel like sticking around for lunch, they offer it from Tuesday to Friday, 11 am to 3 pm.
They offer such meals as Tuna Tartar, Ora King Crudo, Smoked Salmon BLT, and Smoked Salmon Antipasto. You can also get Crab Mac & Cheese, BBQ Hamachi Collar, Bagel & Lox, and Squid Edamame Parfait. If you feel like getting the soup of the day, they have that too!
28. Scarborough Fish & Lobster
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Located on the side of the road on Route 1 is a lobster shack known to have the freshest lobster. There is outdoor seating with umbrellas for cover from the rain or sun.
Some of their popular dishes include clam chowder, lobster roll, or stuffed clams. They also offer a twin lobster plate with two fresh lobsters cooked to perfection.
29. Smiling Hill Farm
The Smiling Hill farm provides high-quality milk, sometimes with a smile on their face to boot! Their milk comes in reusable glass bottles, while the rest of the farm keeps their fields chemical-free from natural fertilizers.
Milk products available at The Smiling Hill farm include classic white milk, flavored milk, and creams. Some of the milk flavors they offer are chocolate, strawberry, coffee, blueberry, vanilla crème, orange crème, and banana milk. Depending on the time of year, you can even get eggnog!
There is more to do at the Smiling Hill Farm than shop for dairy. They host such events as Easter egg hunts, birthday parties, barnyard animal exhibits, and cross-country skiing. Visitors will find something to do in all seasons.
30. Maine Brews Cruise
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Originally known as The Main Brew Bus, this tour was created in September 2012 by Zach and Allison Poole. These tours give behind the scene looks at Maine's craft breweries, wineries, distilleries, and more. You have the choice of not only regularly scheduled tours but also private tours!
If you think you cannot afford a private or corporate tour, fear not because they offer several kinds of public tours. The Maine Brews Cruise offers not only bus tours but also walking and biking tours for those who want to sweat a little.
Those who sign up for these tours must be 21 years and older. This should be no surprise, given that the theme is touring places that create liquor.
Family Friendly Activities in Portland Maine
31. Southworth Planetarium
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Located at the University of Southern Maine, this is an activity suitable for the whole family. With shows of various lengths and topics, you are sure to enjoy your time here and maybe learn something new!
The Planetarium offers a variety of shows, including Dinosaurs at Dusk and Expedition Reef. Rusty Rocket’s Last Blast is a great option if you have little ones. Be sure to check the schedule and calendar of events for things you may be interested in.
They have also offered a 3-D laser show in the past with music. Bands include Pink Floyd, Beatles, and Metallica.
This is a fun activity in the area for children and adults. Check their Website to find out current showings that line up with your visit.
32. Children’s Museum and Theatre of Maine
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Play and learn with the various hands-on exhibits at the Children’s museum. Keep busy all day with the numerous displays for infants, toddlers, and children up to teens.
Exhibits include a water play area, interactive ball sculpture, and an art workshop. Also, check out the Outdoor adventure area where little ones can build, dig, and learn about plants.
Maddy’s theater at the Children’s Museum and Theatre of Maine will be one hundred years old in 2023. They provide entertaining shows for children and families. Be sure to check their calendar for upcoming shows!
33. Maine Escape Games
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📍Map It: 125 John Roberts RD #8, South Portland, ME 04106 | Phone: (207) 274-6007 | Website | Hours: 1:30 pm – 8:30 pm Thursday, Friday, and Wednesday; 10:00 am – 8:30 pm Saturday thru Sunday | Entrance: $32.00, adults, $30.00 under 13
Escape rooms all follow the same format. They are basically a game that has you locked in a room or site of the game. In order to escape, you and your team need to solve puzzles, discover clues, and accomplish tasks before the time is up.
The Maine Escape Games are no different! Choose from rooms like Dr. Gem's Time trap, Southport School for Wizards, and Uncle Ned's Cabin. If you fancy something a little scarier, then The Estate, Alien Invasion, or Escape Your fears.
Some things to know are that children under 18 are allowed but have to be accompanied by an adult. Cell phones are not allowed and will be collected at the beginning and returned at the end of the event.
34. Cumberland County Fairgrounds
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Everyone loves fairs, and the Cumberland Country Fair Grounds are a great place to visit should you find some time on your hands. The fair was first created all the way back in 1869 in the area that is now Greeley High School. It is still going strong today, nearly 150 years later.
When you visit, you will see live entertainment, a pumpkin contest and squash weigh-off, harness racing, and a bunch of other fairground events. It is outside, so plan accordingly depending on the time of year. Weather can be very unpredictable!
35. Payson Park
📍Map It: Edward Payson Park Portland, ME 04101 | Phone: (207) 808-5400 | Hours: Open 24 hours | Entrance: Free
Payson Park is 47.5 acres of fun for the whole family. There are spaces for many sports, such as a lighted basketball court, four tennis courts, 2 Little League baseball fields, two softball fields, and two multipurpose fields.
There's even an artificial ice-skating rink and a snow terrain park, where people can go sledding and skiing in the winter. For younger folks, there's also a playground and splash pad. The park and playground equipment are well-maintained, so everyone can enjoy them for a long time.
The Longfellow Arboretum is also on the grounds, bordered by a tidal marsh. The Arboretum has 116 trees, both native and exotic, and is free and open daily to the public.
The park also features picnic areas and is an excellent place for families and dogs. The Back Cove neighborhood has great views and is exceptionally safe for everyone to enjoy. The road through the park has strict speed limits and stop signs and is patrolled by the Portland Police.
36. The Escape Room, Arts District
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📍Map It: The Escape Room, 492 Congress St, Portland, ME 04101 | Phone: (207) 619-3775 | Website | Hours: 12 pm – 8:30 pm Mon to Thursday, 12 pm to 9:45 pm on Friday, 11 am – 10:15 Saturday, 11:30 to 745 Sunday
Remember earlier on our list where we discussed escape rooms where the object is to solve puzzles, find clues, and ultimately escape the area? You have to do this in a certain time frame, or you lose. The Escape Room in the Arts District is no different and offers yet another escape room experience.
They offer such rooms as The Butcher's Basement, The Lost City of the Jaguar King, The London Blitz, and The Blind Tiger Speakeasy. These rooms have varying degrees of difficulty, so do your research before booking one.
If you are interested in visiting, the price is $25 per person, but on Friday thru Sunday, the cost goes up to $70 for one to two people. Children who want to come need to be accompanied by an adult if they are under the age of 13. Those ages 13 to 18 can attend without an adult but need to have their parent or guardian sign a waiver.
37. Hadlock Field
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Hadlock Field is home to Portland’s minor league baseball team, the Sea Dogs. People of all ages can attend this venue to see the future all-stars up close.
The field provides a family friendly environment with plenty of fresh air. A concession stand is also available with popular offerings from hot dogs to nachos.
38. Maine Narrow Gauge Railroad Company and Museum
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The Maine Narrow Gauge Railroad Company and Museum is the perfect place for railroad enthusiasts. It provides the opportunity to learn about Maine’s unique history.
Families can ride the train down the railroad seven days a week. Entry costs $12 for adults and $6 for children between the ages of 3 and 12.
39. Deering Oaks Park
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Deering Oaks Park is a family-friendly destination for travelers looking to enjoy some time outdoors. The wide open space includes benches, grass, and play areas.
A major point of interest is the splash pad open to the public. Remember to bring your swimsuit to cool off on a hot day!
40. Portland Public Library
Credit: Greg LM / TripAdvisor
A visit to the Portland Public Library is the perfect opportunity for an educational family experience. It is open daily with the exception of Sunday.
The urban library offers multiple levels with a wide selection of books. If you are in the area on a weekday, it is definitely worth it to stop by!