Top 10 Things to do in Portland, Maine

Planning a trip to Portland, Maine. Here are my Top 10 Things to do in Portland, Maine

  1. Ride Your Bike

Six of our 16 Maine Bicycle Tours are day tours of Portland. Our 5 Lighthouse Bicycle Tour is an easy 4 to 5-hour excursion along the shores of Casco Bay that features visits to Bug Light, Spring Point Light, Portland Head Light, and Two Lights. Your guides share Portland’s rich history, and the tour includes Portland’s best lobster roll lunch. Trips run daily from May through October. Bike and Brews tours, as well as tours to islands, are also available. 866-857-9544

Looking for information on cycling? The Portland Encyclepedia at 6 Commercial Street offers bike rentals as well as free maps to lighthouses, breweries and more.

For information on biking beyond Portland Check the state of 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

For those looking to explore Portland by foot, there are many options.

Maine Foodie Tours 207 233 7485 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 Portland’s history and architecture. Maps are available via the greater Portland Landmarks website or at the Portland Observatory which is one of my favorite spots in Portland. The large gray building on the backside of the observatory was my first address when I returned to Portland 20 years ago. I nicknamed it the binging sailor because the floors were warped and would often send me stumbling when I was not paying attention.

3. Drink a Beer

With over 25 micro-breweries distilleries, and kombucheries Portland is a serious booze town.  The Portland Beer Map offers a list of on peninsula locations with hours. The Maine Brew Bus  207-200-9111 offers many different bee tours in Portland and surrounding communities. If wine is more your speed Wine Wise 207-619-4630 offers wine walks and sails featuring a variety of wines and spirits

4. Explore Nature

Our local urban land trust Portland Trails has 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 my favorite walks are:

The Fore River Sanctuary

This 85-acre preserve is the home of Jewell Falls, Portland ‘s only natural waterfall, as well as the site of the former Cumberland and Oxford Canal. The lowland area, where salt and freshwater marsh meet, provides wonderful bird-watching opportunities. Red oak and white pine contribute a 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 be sure to visit the award-winning Rosemont Market for great treats.

Presumpscot River Preserve

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 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 major 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 handrail has been added to a side trail on the south side of the island.

5. Get on the Water

Portland Paddle  207-370 -9730 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  207-749-9619 offers two-hour sails as well as charters and educational tours. Be sure to ask the crew about building the 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.

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 Sunday’s there is reggae at Jones Landing,  Or you can ride the mail boat as it delivers mail, people, and freight to the islands.  The cruise takes about 3 hours and offers wonderful views of Casco Bay. Grab a few beers from Rising Tide, may as well go with the nautical them for the ride.

7 Eat a Lobster Roll

No shortage of good places to find one. Here are my three favorites.

Bite Into Maine-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. The offer six styles Maine, Connecticut, Picnic, Curry, Wasabi and Chipotle. If you are here for a week, you can try them all.

Highroller Lobster 104 Exchange St Portland, ME(207)-560-7351 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.

Eventide Oyster 86 Middle St, Portland, ME  207.774.8538 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 then be sure to wash your lobster roll down with a dozen oysters and some local beers.

8. Eat, Eat, Eat

Tiny little Portland, Maine population 63,000. Was named Bon Appetites “Restaraunt City of the Year in 2018”. There are too many choices to commit to anyone restaurant, so I recommend restaurant surfing having an app and a drink at several locations at each meal.

9. Watch the Boats

My favorite spot for a beer in nice weather is the beer window at Flatbread Pizza  72 Commercial St. Grab a beer, and you will have a front row seat for watching the ferries and water taxis come and go.

10. Mingle with the Locals

Summer is short and brilliant in Maine, so we all try to squeeze every drop out of it. Summer in Portland will have robust farmers, markets, lots of free outdoor music and movies.