Portland, Maine
Maine is a gorgeous state and has diverse offerings. Portland is an excellent place for you to base your trip out of. Stroll through downtown, crack open some lobster, eat delicious potato donuts (they're better than they sound), and see Henry Wadsworth Longfellow's home. Just a short drive away are multiple lighthouses. Drive 45 minutes south and you're in Portsmouth, NH, another great town to explore. Alternatively, head north to Acadia National Park to explore the wilderness.
Many attractions in Maine are seasonal, with some things only being open in the summer months due to tourism or weather (Acadia NP for example often has impassable roads in the winter). Check websites, email beforehand, and/or call ahead to make sure you're planning appropriately.
At the bottom of this post we've included our "Honorable Mentions". These are places that are probably worth checking out, but that we didn't see due to time constraints, COVID closures, or other factors.
Fort Williams Park
This a beautiful park that's free to enter. There you can check out Portland Head Light, Goddard Mansion, old military bunkers, and a food truck. It's located south of Portland and the homes in this area are beautiful. We loved the drive out to the park and enjoyed taking the scenic route back to see more homes.
Portland Head Light
This picture probably looks familiar because it's one of the most iconic New England photo ops. Featured on many puzzles, this lighthouse was commissioned by President Washington himself. It was manned by light house keepers for over a hundred years. The poet Henry Wadsworth Longfellow was known to walk there from his home in Portland to visit with the keepers. His poem, "The Lighthouse" is said to have been inspired by his time there.
Bite Into Maine
The food truck "Bite Into Maine" is often there (check their hours) and offer lobsta rolls like the one pictured here.
Goddard Mansion
While you can't go inside, it's fascinating to walk around this dilapidated mansion. The roof is gone, leaving just the skeleton of this mansion once used as a social venue when military members were stationed here.
Military Bunkers
Climb around two abandoned military bunkers. These were important points of protection, especially during World Ward II as a U.S. ship was sunk bya German U-Boat not too far from here.
Old Port
The heart of Portland is its downtown area called Old Port.
Henry Wadsworth Longfellow's Home
Due to COVID, there were no tours, but usually they offer them inside the home.
Portland Observatory
This is an old signal tower used to communicate what ship was coming into port. It's now an observatory. It was closed due to COVID, but worth checking out regardless of if you can go in or not.
Harbor Fish Market
This is a quick stop, but I love the look of the sign and outside of the store. Inside, you can see the lobster tanks and more oyster species than I knew existed.
HiFi Donuts
Portland is home two two specialty donut shops. HiFi is in the Old Port area and offers a variety of unique flavors and designs.
Flatbread Company
This is a chain, but it's delicious and has excellent service so it's worth mentioning!
Portland Museum of Art
This museum is not very big overall, but it offers many unique pieces including ones from world-renowned artists. Admission is free on Fridays, so try to go then!
Customs House
As far as I know, you can't go in, but is cool to see from the outside!
Victoria Mansion
You can go on tours, but we opted to just take a look from the outside at its unique architecture.
Sherman's Books
Started in the 1800s, Sherman's Books has five locations and is Maine's oldest bookstore. Personally, we prefer perusing used bookstores. However, the staff is great, and we're glad we stopped in.
Walk Around
Like when many downtown areas, a lot of the fun is just walking around and taking it all in.
Mainely Frames and Gallery
In addition to their framing business, this store has literal thousands of maps for sale. Their premium offerings are neatly presented upstairs, but head into the basement for maps galore.
Elsewhere in Portland
These stops are not in Fort Williams or Old Port. However, these first two stops (Bug Light & Red's) are both conveniently located on the way back from Fort Williams.
Bug Light
Cute things come in small sizes, and Portland Breakwater Lighthouse, aptly known as "Bug Light", is no exception. Visiting this spot offers great vires of Fore River and of Portland (the lighthouse is in South Portland).
Red's Dairy Freeze
Excellent soft serve, shakes, and sundaes!
Hadlock Field
The Portland Sea Dogs, the AA affiliate for the Red Sox, play here. Tickets are cheap. We loved sitting in right field as there was a bar top in front of the seats which made it easy to eat while watching. Minor league games are more laid back than professional ones. In between plays we could hear the right fielder talking to fans or to the players in the bullpen behind him.
Holy Donuts
These are delicious potato donuts. These are cakier than your average donuts and come in a variety of unique flavors.
As I mentioned, Portsmouth is only a 45-minute drive from Portland. In addition to marking another state off your bucket list, Portsmouth offers a number of attractions:
The home of John Paul Jones
A beautiful market square with a historic church, bookstores, and restaurants
A historic and beautiful library called The Portsmouth Athenaeum (limited hours, so check ahead)
Colby's Breakfast and Lunch is a delicious and cheap place to eat. The staff is incredible.
Nubble Light
On the way between Portland and Portsmouth is Nubble Light in York. It's worth the short detour.
Transportation
Flights into Portland can get on the pricier side, but we were able to find some reasonable tickets. Portland Jetport only has one terminal, so you're going to be hard pressed to find direct flights unless you're on the East Coast. A cheaper option may be to fly in & out of Boston. You could rent a car and be in Portland in three hours. This may work well if you're already looking to make multiple New England stops.
Important: Make sure you book your flights into Portland, Maine (PWM) and not Portland, Oregon. I had to really watch for this when looking into flights.
Lodging
We stayed in an Air BnB but did not have a great experience with that host, so we don't have any recommendations there. We did note that if you avoid peak travel months (June-August), you can sometimes find cheaper AirBnB rates. That comes with the tradeoff of potentially some seasonal attractions being closed.
Honorable Mentions
There's a lot to do in Portland. Here's a few things we didn't get a chance to check out due to COVID or time constraints but that may be work checking out:
Casco Bay Islands
Fort Gorges
5th Maine Museum
Allagash Brewery
Osher Map Library and Smith Center for Cartographic Education