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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.





Bike Maine Lodging

We are happy to partner with the Bicycle Coalition of Maine again to provide a lodging package for the 2019 Bike Maine event. Space is limited so book today.

Bike Maine Lodging


E Bikes Available

We have e-bikes available on some of tours look for this symbol.

e-bikes available


Gift Certificates Available

We have gift certificates for all our trips or in any amount. Why not give your loved ones lasting memories this holiday season.  Our day trips in Portland are popular gifts. Give em The 5 Lighthouse Tour, Bike and Brews or new Pedal Peak’s Island Tour.

Gift Certificates for day tris can be bought on that tour’s page. To buy a gift certificate for a specific dollar amount. Give us a call 866.857.9544



Hall of Fame

Happy to have earned the TripAdvisor “Certificate of Excellence” for the 5th straight year and to join the Hall of Fame.


Best Places to Eat a Lobster

We are often asked, Where is the best place to get a lobster.  Here are 3 of our favorites
Five Islands Lobster
Located in Georgetown Maine just south of Bath, Five Islands is a great place to visit after a long day at Popham Beach.
1447 Five Islands Rd. Georgetown, ME 04548
Miller’s Lobster 
Tucked away in Spruce Head, Miller’s is a family-owned lobster shack with wonderful views  and great homemade deserts.
92 Eagle Quarry Rd. Spruce Head, ME 04859
Located on the quiet side of Acadia, Thurston’s tag line is “From the Sea to Your Plate.” For five generations, the good folks at Thurston’s have produced great food in a wonderful setting.
9 Thurston Road – Bernard, ME 04612

688 Million Reasons to Buy Local


My favorite statistic from the Buy Local movement is that 75% more money stays in the local economy when you buy local. It makes sense, a dollar spent at Bard, Tandem, Yordprom or any other locally owned coffee shop will only travel as far as the owner’s pocket whereas a dollar spent at Starbucks travels across the country to corporate headquarters, where it is then dispersed among employees and ultimately shareholders.

Portland is many things, including a robust tourist town. In 2015, 5.5 million people visited Portland, creating an economic impact of $688 million dollars. Portland is also a town with an award-winning food culture. The reality is that a tiny town of 66,000 people can’t support Portland’s restaurants. We need the tourists. People travel for a variety of reasons, but one thing that unites all travelers in the desire for a unique experience. From a sampling of oysters at Eventide to the thrill of getting your picture taken with Mickey Mouse and everything in between, experiences create memories.

The Maine Office of Tourism has done a wonderful job of identifying the profiles of the most common visitors to Maine and has focused their marketing efforts on the three largest groups: balanced achievers, genuine originals, and social sophisticates. All come to Maine seeking experiences that support their values and desires.  Genuine originals value outdoor recreation, social sophisticates value excellent accommodations and balanced achievers value checking things off their bucket lists. Yet among these three distinct groups of travelers, the one thing that unites them is their desire to connect with what is local and unique. If you ask people what their most poignant vacation memories, I doubt many will say the awesome Baby GAP store

We are fortunate to live in an amazing place, with great natural beauty, an abundance of locally sourced food, and a strong and friendly community. Where you buy your morning coffee goes beyond feeling good, it helps sustain the unique community that draws the tourists who in turn bring $688 million dollars a year to Portland. This is money that among other things, allows our food and beer scene to thrive and attracts the wonderful mix of people of diverse, skills, races, and beliefs who have lived and traveled all over the world and yet choose to make Portland their home.


Where to Eat in Portland, Maine

The number one question we get asked is “Where to Eat in Portland, Maine?” Odds are if you are coming to Portland you have heard about our amazing food scene and all our award-winning restaurants like Eventide, Fore Street, and Central Provisions.  All great restaurants that I tend to avoid in the summer because they are so hard to get a table at. So here are a few local favorites that are easier to get a table at.

Back Bay Grill-many long-time residents will tell you that this is their favorite restaurant in Portland 65 Portland Street 207.772.8833

David’s-Another Portland icon. David’s has been in Portland in one form or another for over 25 years. Seasonally he operates David’s Opus Ten featuring a multi-course prix fixe menu. It is my favorite fine dining experience in Portland. 22 Monument Square 207.772.8833

Isa- describes themselves asa cozy neighborhood bistro serving an eclectic yet seasonally driven menu. The dishes are influenced by the places we’ve been and the things we love.” A newcomer to the Portland food scene Isa has quickly become a favorite. 79 Portland Street 207.808.8533

Another challenge in such a food-centric town is finding good casual fare.  here are a few casual places where you will often find us eating and drinking.

Bonobo great pizza with both traditional and eclectic toppings, Bonobo is comfortable neighboorhood spot in the west end. 46 Pine Street 207.347.8267

Mash Tun in the heart of the old port, Mash Tun offers a great $6.00 grass-fed burger and a big selection of local and not so local craft beers. 29 Warf Street

Silly’s another Portland icon, Silly’s has a broad menu with good choices for vegetarians and vegans as well as super laid back vibe making it a great choice for families with younger kids and people who cannot agree what they want to eat. 40 Washington Av 207.772-0360

There is something for everyone in Portland’s dining scene.