Planning a trip to Portland, Maine? Good choice. Portland offers a perfect blend of outdoor activities and small-town charm.
Think of Maine and you’ll probably think of iconic lighthouses perched on rocks above dramatic seas. You’ll think of fresh lobsters, indie businesses, and sailboats in the harbor. Well, Portland has all of that and more.
Whether you want to spend a few lazy days soaking up the atmosphere and sampling local craft beers, cycle along stretches of stunning coastline, or take to sea for an epic sailing adventure, you’ll have a wealth of options.
Read on to discover 10 of our favorite things to do in Portland, Maine. And while you’re here, please check out our full selection of Maine Bicycle Tours and Walking Tours.
1. Ride Your Bike
Six of our 14 Maine Bicycle Tours are day tours of Portland because not only does Portland make for a perfect basecamp for exploring Maine, but it’s an excellent town to visit in its own right. There’s so much to discover in the Portland area, and there’s no better way to do it than by bike!
Our 5 Lighthouse Bicycle Tour is an easy 4 to 5-hour excursion along the picturesque shores of Casco Bay that features visits to Bug Light, Spring Point Light, the famous Portland Head Light, and Two Lights. This is postcard-perfect Maine – magnificent coastal scenery and historic lighthouses.
Expert local guides will share with you Portland’s rich history, and you’ll get a real taste of local culture when we stop for Portland’s best lobster roll lunch. Trips run daily from May through October.
If a biking day trip in Maine is what you’re looking for, browse our full selection of Maine Bicycle Day Trips.
Need more info on cycling in the Portland area? The Portland Encyclepedia at 6 Commercial Street offers bike rentals and free maps to lighthouses, breweries, and more.
For information on biking beyond Portland, check out the Maine Bicycle Book featuring route notes for rides throughout Maine and the East Coast Greenway, which has mapped a route from the Canadian border to Key West, Florida.
2. Go For a Walk
Rather explore Portland by foot? There are many options available.
Maine Foodie Tours offers a 2 to 2.5-hour Culinary Walking Tour of Portland that features local seafood, cheeses, and beers, as well as happy hour tours and boat tours.
Looking for independent exploration? Greater Portland Landmarks offer a multi-part set of maps that offer walking tours of historic Portland, featuring stories from Portland’s past and an insight into the town’s architecture. Maps are available via the Greater Portland Landmarks or at the Portland Observatory, one of my favorite spots in Portland.
And, of course, you can also join us at Summer Feet for one of our own Maine Walking Tours. Our multi-day walking vacations explore Portland and other unforgettable destinations in Maine, including the White Mountains and Acadia National Park.
3. Drink a Beer in Portland, Craft Beer Capital
With over 25 microbreweries, distilleries, and kombucheries, Portland is a seriously boozy town and has been voted as one of the country’s best towns for beer. Head over to Mainer for their Brewery Map to find an extensive list of Portland, Maine Breweries. Many of the breweries will welcome visitors and offer tours and tastings.
The New England beer scene has been booming recently, and Portland is a real hotspot for any beer enthusiast. Visit a few taprooms across town, and you’re sure to be delighted by the variety of beer on offer. The number of options can almost be overwhelming, but fortunately, the kind guys at Thrillist have put together a handy list of some of their favorites: The Best Breweries in Portland, Maine.
At Summer Feet, we’re always happy to stop for a craft beer, especially after an energy-burning cycle. That’s why we put together our own Pedals and Pints tour – join us for fantastic scenery, local food, and top-quality local beer.
Looking for further options? The Maine Brew Bus offers many different beer tours in Portland and surrounding communities. And if wine is more your thing, Wine Wise offer wine walks and boat trips featuring a variety of wines and spirits.
4. Explore Nature
Our local urban land trust Portland Trails has created and maintains over 70 miles of trails within Portland. Their website features an interactive map, or you can purchase a paper version at many locations in town. Some of our personal favorite walks are:
This 85-acre preserve is the home of Jewell Falls, Portland‘s only natural waterfall, and the former Cumberland and Oxford Canal site. The lowland area, where salt and freshwater marsh meet, provides fantastic bird-watching opportunities.
Red oak and white pine contribute habitat for many songbirds and small mammals in the upland area. The land around the falls was donated to Portland Trails by the family of Tom Jewell, one of Portland Trails’ founders. Open from dawn to dusk, year-round
If you enter from the Brighton Avenue side, visit the award-winning Rosemont Market for great treats.
This exceptionally beautiful trail follows a deep ravine away from the residential neighborhood and into the Preserve. The trail is very steep in places. Boardwalks and bridges pass over wet areas while allowing for mountain bike access.
Once the trail reaches the river’s edge, signs direct the visitor upstream or downstream, both offering spectacular river views. Upstream, the trail features several short loops into wooded, upland areas. That trail continues along the shoreline under the highway overpass for another ¾ mile.
Downstream, the trail crosses through property protected by the Falmouth Conservation Trust before it reaches Presumpscot Falls. The trail includes a portage to help paddlers around these swift rapids. Please respect private property at the end of the trail.
Mackworth Island is a legislated bird sanctuary and is connected to Falmouth by a causeway at the mouth of the Presumpscot River. It is the former home of James Phinney Baxter and his son, Governor Percival Baxter, and was deeded to the State of Maine in 1943. Currently, it is the site of the Baxter School for the Deaf.
The island is open to visitors from dawn to dusk. The perimeter path is maintained by the Maine Bureau of Parks and Lands. A detailed trail map can be borrowed from the guard at the gatehouse near the parking area. An outhouse is also available in the parking lot.
This easy trail circles Mackworth Island and offers excellent views of Casco Bay. The trail surface is wood chips and packed soil, which may be slippery when wet, but the terrain is generally level, with moderate slopes not exceeding 10%.
There are no steps or other significant barriers to wheelchairs on the main loop. Small side trails follow steep slopes to the shore and may be inaccessible to some visitors. A new staircase with a handrail has been added to a side trail on the island’s south side.
5. Get on the Water
When you’re in Portland, it’s definitely worth getting out onto the beautiful coastal waters for a boat trip. Maine has a rich maritime history, and when you explore a town like Portland, it’s hard not to get a little sea fever and crave adventure!
Portland Paddle offers kayak tours and stand-up paddleboard tours from the East End Beach. Many of their tours visit Fort Gorgeous, a Civil War-era fort in the heart of Casco Bay. They also offer SUP yoga classes and kayak rentals for experienced paddlers.
Maine Sailing Adventures offers two-hour sails as well as charters and educational tours. Be sure to ask the crew about the building of their boat, which they did in Casco Bay. Stop by Black Tie Catering on Commercial Street for a bottle of wine and great snacks for your sail.
And if you fancy having an adventure with Summer Feet, our six-day Trails, Ales, and Sails tour features both sailing and kayaking activities.
6. Visit an Island
There are over 100 islands in Casco Bay. Casco Bay Lines offer ferry service to all the populated ones.
Peaks Island is a short 20-minute ferry ride from Portland but offers a great island vibe. On Sundays, be sure to catch the reggae at Jones Landing.
You can also get to the island by riding the mail boat as it delivers mail, people, and freight to the islands. The cruise takes about 3 hours and offers terrific views of Casco Bay. Grab a few beers from Rising Tide (might as well pick a beer with a nautical theme for the ride!).
7. Eat a Lobster Roll
There is no shortage of good places to find a lobster roll in Portland, Maine! Here are three of our favorites.
Bite Into Maine
Our good friends Carl and Sarah make award-winning lobster rolls at their original food truck located at Fort Williams Park in Cape Elizabeth and the Allagash brewery. They offer six styles: Maine, Connecticut, Picnic, Curry, Wasabi, and Chipotle. We’d recommend a particular style, but they’re all delicious. If you are here for a week, you can try them all!
Highroller started as a food cart just a few years ago. Last year they expanded into an inviting space on Exchange Street in the heart of Portland’s Old Port. Not only do these guys serve great food, they also have an amazing selection of beers.
Eventide Oyster
The brown butter lobster roll here is smaller than a traditional lobster roll, but every bite explodes with flavor. Plan on waiting for a table, it’s always a choice with locals. But we’re sure you won’t regret the wait. Wash your lobster roll down with a dozen oysters and some local, craft beer goodness.
8. Watch the Boats in the Bay
Enjoy some relaxation as you watch the boats on the bay.
When the weather is nice, there’s no better spot to sit and have a beer than by the window at Flatbread Pizza on Commercial St.
Watch the ferries, and water taxis come and go and enjoy a moment of real peace and quiet on your vacation. The beauty of Portland is in the pace of life. Let the sea work its magic and provide you with some much-needed revitalization. Enjoy your food and drinks as you watch the world go by…
9. Eat, Eat, Eat
Aside from winning plaudits as one of America’s best towns for beer, tiny little Portland, Maine, population 63,000, was named Bon Appetites “Restaraunt City of the Year in 2018”. But lobster rolls aren’t the only tasty food on offer…
Despite its size, Portland thrives with creative energy, and here, you’ll find a blend of exciting new businesses and tried-and-tested local favorites. Indulge in local specialties and excellent, fresh seafood, or branch out and try something new at one of the town’s restaurants that specialize in international cuisines. There are many options to explore, from Middle Eastern street food to Japanese ramen.
There are much too many places we love to select any one restaurant, but you can consult Boston Magazine’s choice of 10 of their favorite Portland restaurants for inspiration. We recommend doing your research based on what you like and stopping in different places for drinks to soak up the variety of atmospheres.
10. Mingle With the Locals
Our final choice of things to do in Portland, Maine is the simplest of all: get to know the locals. Portland is an incredibly welcoming town, where people are often happy to pass the time of day or give you recommendations for your travels.
We’re all pretty proud of our town and love to share it with guests. If you’re traveling during the summer, you’ll be able to enjoy excellent markets, free music concerts, and outdoor movies.
Check the latest listing at Portland Downtown to see what’s on.
This brings to a close our blog on just some of the best things to do in Portland. If you have any questions about this article or any of our tours, please get in touch.
