Things to do in Portland, Maine

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 Casco Bay’s shores that features visits to Bug Light, Spring Point Light, Portland Head Light, and Two Lights. Your guides will share Portland’s rich history, and the tour includes Portland’s best lobster roll lunch. Trips run daily from May through October. We also offer bike and brews tours, city tours, and tours to the islands. 866-857-9544

If you are looking for information on cycling? The Portland Encyclepedia at 6 Commercial Street offers bike rentals and free maps to lighthouses, breweries, and more.

For information on biking beyond Portland, The Bicycle Coalition of Maine’s Where to Ride page features route notes for rides throughout Maine. The East Coast Greenway has mapped a route from the Canadian border to Key West Florida.

  1. 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

Want to explore Portland on your own? Greater Portland landmarks offer a multi-part set of maps that provide 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, one of my favorite spots in Portland. The large gray building behind 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.

  1. Drink a Beer

With over 25 micro-breweries, distilleries, and kombucheries, Portland is a great 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

  1. 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, and the site of the former Cumberland and Oxford Canal. The lowland area, where salt and freshwater marsh meet, provides excellent 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 Tom Jewell’s family, 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 stunning 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 maybe inaccessible to some visitors. A new staircase with a handrail has been added to a side trail on the island’s south side.

  1. 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 terrific views of Casco Bay. Grab a few beers from Rising Tide, you may as well go with the nautical theme 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 at Fort Williams Park in Cape Elizabeth and the Allagash brewery. They 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.

  1. Eat, Eat, Eat

Tiny little Portland, Maine population of 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.

  1. 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.

  1. 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.








5 Questions About Self-Guided Bike Tours

The COVID-19 pandemic has accelerated an already fast-growing trend in adventure travel the rise of the self-guided bike tour.  Summer Feet Cycling was a pioneer in the self-guided tours launching our first self-guided bike tour, Pedal the Coast Self Guided (SG) in 2003. Here are answers to the five most common questions about self-guided bicycle tours.

  1. What if I get lost?

Over the years we have had several guests creatively route themselves as we like to call it. Fortunately, technology makes this harder.  We have partnered with Ride with GPS to use their “experiences” product for all our self-guided tours.  The experiences product allows us to load turn-by-turn directions which you can follow using the Ride with GPS app on your smartphone. The best part is that since the app is following a GPS track and using the GPS built into your smartphone no cellular data is needed or used. In addition, we still provide paper route notes and maps to all guests. If the app and map still leave you confused, you can always ask a local for directions. One of the joys of travel is getting to meet new people.

2. What If I Have Mechanical Issues?

We thoroughly check all bikes before sending them out on a self-guided tour but sometimes things still go awry. On every trip, we equip you with the tools you need to handle minor mechanical issues, spare tubes, a pump, tire levers, and multi-tool. On the day-to-day details that accompany your route notes, we list the name and address of any bike shops you might pass during your ride and in a pinch, you can call our office, and often we can walk you through fixing your bike via facetime.  In the event of a major mechanical failure which has happened only a handful of times, we will arrange to get you a replacement bike.

3. What if it rains?

Like all our guided tours, self-guided tours run rain or shine. In the event of extreme weather like a hurricane that threatens your safety we will find a way to transport you. Otherwise, we do provide the telephone number of local cabs and transportation companies if you wish to arrange transportation to your next hotel.

4. What Will I See?

Our daily summaries provide you information about some of our favorite sites on each day’s ride. But, one of the great things about a self-guided bike tour is the freedom to explore. Since you are on your own you can take time to hike a path, linger in a coffee shop, sit by the ocean, or explore a local art gallery. If ice cream is your thing stop at every ice cream shop.ere  Like craft beer?  There will be plenty of opportunities to stop and find your favorite.

5. Is a Self-Guided Bike Tour Right for Me?

For most people, the answer is yes. Are you an adventurous and independent person? Then a self-guided bike is right for you. You will get the benefit of our years of living and working on the coast of Maine with the freedom to make it your own vacation. If you are comfortable with the daily mileage then a self-guided bike tour is a great fit.






Risk Free Reservations

Like everyone, we miss travel and anticipation of travel. To help people plan their 2021 vacations, we are offering risk-free reservations.

Multi-Day Bike Tours

For all multi-day tour departures for 2021, we are offering fully refundable deposits. Book your 2021 cycling vacation today, and your deposit will be fully refundable if you cancel by May 1, 2021. Deposits on all multi-day tours will be fully refundable up until May 1, 2021.
After May 1, 2021, if you have to cancel a trip between 60 and 31 days before departure, participants can request a refund less the $150.00 per person cancellation fee or receive a 100% credit for future travel.  For cancellations between 30 and 15 days before departure, participants will receive a 100% credit for future travel. Cancellations 14 days or less from departure cannot be refunded. If the cancellation is due to government-mandated shutdown participants will receive a 100% credit for future travel.

Day Trips

Day trips require a $50.00 per person deposit, which is fully refundable if you cancel at tour up to 48 hours before departure.


Tour for Tips -Free Bike Tours

For June, we will be offering several of our local Portland tours for free using the “Tours For Tips” program. The premise is simple; you get a free bike tour from an experienced local guide at the end of the tour; you tip the guide for their time and effort. We will be offering three tours under the tours for tips program: Around the Peninsula, Three Lighthouse Tour, and Bike and Hike.

Around the Peninsula

The trip begins with an easy ride along the Eastern Promenade bike path. We will stop along the path to learn the history of Casco Bay and the Calender Islands as well as the life story of George Cleeve, Portland’s lawsuit-happy co-founder.

The next stop is Back Cove and Portland’s Deering neighborhood. It was created in the 19 Century by wealthy residents angry about Portland’s rising property taxes.

From Back Cove, you cycle into the Portland’s West End. Historically, the swanky part of town, the West End features broad tree-lined streets and beautiful homes from Victorian to Shingle Style.


The Three Lighthouse Tour

The three lighthouse tour is a variation on our best selling and award-winning 5 Lighthouse Tour.

Our signature day trip. Enjoy gentle cycling along the shores of Casco Bay. See three lighthouses, wander the coast, get great views of Portland, Casco Bay, and the open ocean. Your friendly and knowledgeable guides will teach you all about Portland’s rich history. The free tour does not include lunch but you are welcome to pause for a lobster roll.

Bike and Hike Tour

Your leaders will meet you at the Ocean Gateway Visitors center in the heart of downtown Portland. After a brief safety talk, we will hop on our bikes and pedal along the Eastern Promenade.  We will stop to learn about Ft Gorges, Bug Light, and the Calendar Islands before cycling into Falmouth and Mackworth Island. Here we leave our bikes for the one-mile walk around the island.  You will enjoy stunning views of Casco Bay and visit the cemetery where Governor Baxter buried his dogs. After hiking, we hop back on the bikes and pedal back along the ocean to Portland.


What is Included:

Experienced Guide
Bike and Helmet if needed


The Details

Tours can be booked by calling Summer Feet at 866-857-9544
All participants must sign a waiver ( we will email it yo you, and you can scan and send it back)
All tour leave from the Ocean Gateway Visitor Center
Tours typically start at 10:00 am, but this can be changed.
Tours will follow Maine CDC social distancing guidelines.
All participants must wear masks.
Guides can be tipped via cash or Venmo.




Risk Free Reservations

We are preparing for the start of the 2020 bike tour season, although we do now know exactly when that will be.  Summer Feet Cycling is committed to the safety of all our guides and customers, and we will make all necessary changes to our operating procedures to ensure everyone’s safety. I keep in touch with all our staff, and I know that they are looking forward to getting out on their bikes with customers in the not too distant future.

We all feel stuck in limbo waiting to see how the trajectory of the virus unfolds and how it impacts our collective futures. To help people plan their summer travels and to give our customers something to look forward to, we are offering risk-free reservations.

For any day trip booked in 2020 for 2020, you may reschedule to any other date in 2020 up to seven days before the tour date or elect to receive a full refund of the amount paid less the $5.00 per person cancelation fee.  Alternatively, you can place the funds on a gift card that never expires and receive a 20% bonus added to the card. A quick example: if you paid a $100.00 deposit, the value of the gift card would be $120.00.

For multi-day tours, you can reschedule your departure to any other date in 2020 up to thirty days before departure. Alternatively, you can choose to places the funds on a gift card that never expires and receive a 20% bonus added to the value.

We are looking forward to summer, sunshine and bike rides.


Cyclists with ocean behind him in Portugal

5 Lighthouse Tour Portland Maine

Since we started our Five Lighthouse tour in Portland, Maine, guides have actively debated how many lighthouses we see on the Five Lighthouse Tour. One would think the answer is five, but it depends on what qualifies as a lighthouse and how much of the lighthouse do you see.  Initially, there were two lighthouses at Two Lights hence the wildly original name. One of the lighthouses was decommissioned in 1924. So there are two towers at Two Lights but only looks like a lighthouse today. Does that count as a lighthouse?

Just beyond Portland Head Light is the Ram Island Ledge Light? You can see it clearly, but we do not count it among one of the five. We count the five as Bug Light, Spring Point Ledge, Portland Head Light, and Two Lights making Ram Island the 6th, which is 20% more lighthouse viewing.

If you take the tour on a wicked clear day, then you can glimpse Half-way Rock Light 10 miles away in Casco Bay, bringing the total to 7.

Since we cannot dazzle our guests with our sparkling personalities and our knowledge of all things Portland and lighthouses, here is a virtual Lighthouse tour.  Featuring photos of the lighthouses since the governor of Maine has told us to Stay Home and a few fun facts about each.

Bug Light

The official name is the Portland Breakwater Light, but locals have always referred to it as “Bug Light” because it is cute as a bug. At only 37 feet tall, it is one of the smallest ocean lighthouses in the country.

Small Lighthouse South Portland Maine


Spring Point Ledge

The lighthouse was constructed in 1897. The rock causeway leading to the lighthouse was added in 1951. Initially, the lighthouse was an island with two men living in it, a lighthouse keeper and an assistant lighthouse keeper.  If they wanted to exercise, it was 56 times around the deck to walk one mile. Rumor has it one keeper forgot to shut the hatch before setting out for his walk, which why many keepers chose less athletic hobbies like carving duck decoys.

Caisson Style Spring Point Ledge Lighouse


Portland Head Light

It is big, famous, old, and It was commissioned in 1791. You could argue it was the first lighthouse built in the United States. Yes, there are older lighthouses on US shores. They were constructed before the United States ratified The Constitution, creating what we now know as the United States of America. George Washington was personally involved in designing the lighthouse, and he urged the builders to use local stones to reduce construction costs. Captain Joshua Strout become the keeper in 1869 with his wife Mary as the assistant lighthouse keeper. When they retired, their son Joseph became the Lighthouse Keeper. Between them, they served for fifty-nine years.

Portland Head Light and Keepers House

Ram Island Ledge

I often say lighthouses were not built with foresight. Many lighthouses were built as a result of maritime disasters.  Ram Island was one of those, near Christmas in the early 1900s, a steamship headed for Boston, and New York crashed into the ledge. As a result of this tragedy, a lighthouse was built on the ledge. During the winter of 1949-1950, Joe Johnson, the assistant keeper, spent forty-five straight days on the ledge because the weather was too bad to bring out his replacement.

Moon rises behind Rame Island Ledge Lighthouse in Maine


Halfway Rock

Halfway Rock was another lighthouse not built with foresight.  An escalating series of maritime disasters led to the building of the light. It is an eleven-mile row from the island to Portland, meaning the keepers were often stuck on the rocky ledge for weeks at a time. When Half-Way Rock came online, the bureaucratic minions at the Lighthouse Commission in Washington, DC, decided that the Portland Head Light was not as essential, and they ordered it shortened by twenty feet.  There was an outcry, hullaballoo, and even a little ballyhoo from area residents, and Portland Head Light was restored to its original height one-year later.

Halfway Rock Lighthouse Maine

credit: Pat Smith Dreamstime


The two lights were built to make these lighthouses distinct from other lighthouses in the region.  In January 1885, keeper Marcus Hanna saved two sailors from icy seas, and six months later, he was awarded a “gold lifesaving medal.”

Lighthouse Tower in Cape Elizabeth, Maine


There are many more fun facts about Portland and the lighthouses on the 5 Lighthouse tour. Hopefully, we will see many people on tour soon. Until then, stay safe.




Bike Maine Lodging and Transportation

We are happy to partner with the Bicycle Coalition of Maine to provide lodging and shuttle service for cyclists who want to join in the fun of BikeMaine but prefer not to camp. Our premium service will book your hotels, provide a shuttle between the BikeMaine Village and your lodging as well as deliver your bags to your rooms. Join us and the Bicycle Coalition of Maine on the 2020 BikeMaine ride.


  • Price Per Person $1175.00 double occupancy. Does not include Bike Maine Registration
  • Single Supplement $350.00

More information about the 2020 Bike Maine ride can be found here Bike Maine


Save 20% on North Macedonia

As part of our 20th-anniversary celebration, we are offering several special departures at a 20% discount. The first tour is our North Macedonia departure on June 7-14, 2020.

Check out the tour here  North Macedonia

Byzantine Church overlooking Lake Ohrid, Macedonia Two cyclists on a country road with hills in the background A variety of colorful salads