Lovely visit to the Portland Observatory…read more We had intended on a self-tour but were told that self tours would start at 4:30pm...and that before that time, you would have to take a toured guide up the tower. As there was a scheduled guide about to start soon...we opted to take the guided tour. At that time (mid-week in late August around 12pm) there were only four of us on that tour. Our tour guide, an older woman, was wonderful. As we ascended the tower during the 45-minute tour, we stopped off at each floor and she explained a bit about the tower and its history. Lots of interesting facts! We made it to the top to take in some amazing views of the area. Tours are $10 for adults, $5 for ages 6-16 and free for those 5 and under. The stairs (there are about 100) throughout the tower are spiral-ish...so be careful of your foot placement on the narrowed parts of each step while ascending and descending. Street parking signs can be a bit tricky in the area reading "...no parking on the 1st/2nd/3rd/4th ___day of the month..." Be sure to properly read those signs and park accordingly.

My plans only have me in town for two days, so I asked my local coworker one sight I had to see…read morewith a short time frame, and was sent here. Just a fun little local tip. The history itself is cool enough: this was a lookout for ships coming into the harbor before radio, and is the oldest currently standing in the USA. But I really appreciated the elevation for getting a good look of the downtown and harbor area, walking around the tower in the breeze and seeing the ocean peaking through the islands in the harbor. Worth the $10 to the top. (Note: the stairs are steep and there's no room inside for an elevator. We're talking large curving internal staircases. Maybe not for those with mobility issues.)

Fort Gorges at Portland Maine in Casco Bay. This is old Civil war Fort you can access by boat and…read moreexplore! We did not get to go there! Noël Teel Lisa Diane Boyce-Vanoy Dale Lisa Vanoy Tony Vanoy #newengland25trip

Although I can't speak to Fort Gorges unless it's from the perspective of someone who's seen it…read morefrom a distance countless times, it is a beautiful landmark in Casco Bay. I hope to one day visit via kayak, but for now I'll settle staring at it from the port bow of the ferry.

Congress Squark Park, an open and public concrete space - and home to Union Station Clock -, was…read morecreated through an urban renewal project in the early 80's. Thankfully, the NPO Friends of Congress Square Park have done a lot over the years to protect it from outside buyers, preserve it, and breathe new life into it. This once deteriorated space has become a hub for arts, entertainment, and community togetherness. Over the course of the past many years I have... - Been entertained by the Circus Conservatory of America - Listened to the Maine Marimba Ensemble perform - Watched fire jugglers - Looked at art - Played an impromptu game of kickball ... in the park. And that was before all of the great things that are now intentionally planned for the space! Now, there's... - copious amounts of lovely seating - food trucks - even more musical and theater performances - outdoor movies - dance lessons - group knitting sessions - yoga and tai chi - kid-friendly activities ... all in the park. So impressed and grateful towards the Friends of Congress Square Park for what they've done. Bravo, folks! Thank you!

Adorable little park with incredible public space offerings & events throughout the year.read more

This was my "go-to" park for jogging in the morning during a July 2026 stay in South Portland. It…read morehas so many pluses. First, parking is free and generally available in the morning. Second, it has a lovely, open view of Casco Bay with several islands in the distance. Third, you can jog along the park and around the marina - or connect to the Greenway trail for a longer run. Fourth, it has a cool display on WW2 history and Portland's vital role in navy shipbuilding (more than 25,000 workers added to the population).

This is a nice place for a quick stop! Theres a nice walking path. If it was a warm day i would…read morehave taken a walk since it has beautiful views. The lighthouse itself was small but well kept. Overall a nice picturesque park.

Headed over to Fort Williams Park to see the Portland headlight, which is the oldest lighthouse in…read moreMaine authorize by George Washington. There are several paid parking lots, which is a short walk to the water to see the lighthouse. They have a small gift shop adjacent to the lighthouse. There are several food trucks around the area where you can purchase food and dine on picnic tables or on the grassy area. Also, you can walk a path along the waters edge to get a good view of the rocks and ocean. It's so beautiful and relaxing. We ended up walking around for about two hours. I highly recommend visiting Portland, headlight and enjoying the beautiful views.

Our family visited Portland Head Light (in Fort William Park) to take photos around 6pm in July…read more2026. It's about a 10 minute drive from South Portland and well worth the trip! First, it is the oldest lighthouse in Maine (which was completed in 1791 and authorized by George Washington). Second, it's easily accessible - just a short walk from the parking lot. Third, you have the option to buy lobster rolls if it's lunch or dinner time or bring your own picnic to spread out on the spacious grounds. Parking is only $3 per hour. Since the WiFi connection for Verizon was weak, I paid for a printed paper ticket (minimum of $6 for 2 hours). Would strongly recommend coming here within 2 hours of sunset for the best lighting of photos. Also, be sure to spend some time walking along the coast for stunning views of the rocks below.

Relaxing park with a view cool breeze and walking trails. So very relaxing to exercise walk work or…read morejust take in the scenery.

This park was a great find with plenty of area to enjoy. Please note, there is limited amount of…read moreparking. I didn't realize this importance of this area until I had read the plaque. Great memorial to the USS Portland. Yes, there are still couple of cannons. The views are beautiful overlooking the ocean. If you have time, take the stairs to the wooded area and to the water. Enjoy this great park.

"General opinion's starting to make out that we live in a world of hatred and greed, but I don't…read moresee that. It seems to me that love is everywhere. Often, it's not particularly dignified or newsworthy, but it's always there - fathers and sons, mothers and daughters, husbands and wives, boyfriends, girlfriends, old friends... If you look for it, I've got a sneaky feeling you'll find that love actually is all around." This quote, from none other than Prime Minister Hugh Grant of "Love Actually" perfectly explains Love Locks here in Portland. Up until February 2013 it was just a fence... a nondescript fence that hundreds of thousands of people passed every year without a second glance... until one night some drunken friends decided to buy padlocks, write a dedication to a loved one on it (for one of the original women, that included her husband and two dogs), lock it on the fence, then dispose of the key. Portland has such a European (where this idea originated from) feel to it, that it only makes sense for us to have our own version of Love Locks, too! Some folks think it's an eye sore... I think it's lovely. So lovely in fact that I may or may not have a lock up there myself (and I may or may not have thrown my key over the fence into the ocean... which I now realize isn't entirely eco-friendly. Dear fishies, please be careful grazing on any new sparkly snacks you might have recently found!). What can I say? I love love. And I love the ocean. And I love this city. And I love romantic gestures. And I love the strong bonds people have with other people, places, and pets. And I love unique forms of art. And I love pretty things. Don't you? Who knows if our Love Locks will stand the test of time. If, over the years, the locks begin to rust and become an eye sore instead of love lore, I would think the city might take it down. So come leave a lock of love for your loved one (be that your mom, your sister, your pet rabbit, your favorite coffee drink, or yourself) now... or at least take the time to read some of the proclamations of passion permanently padlocked here in Portland!

They're locks... on a fence. That's 5 stars right there. haha They're right in the middle of the…read moreOld Port and it was cool seeing it since I've never seen a love locks fence before in person. It is small and insignificant for most, but for it to have a yelp listing -- I had to check it out. They are tons of locks on it and most of them looked recent with in the year. That poor fence is holding on for dear life. If you're a lover want to lock it in -- put a lock on the love locks fence to make it official. That's more lasting than facebook official. Story has it that once you lock it up, that you toss the key in the water over the fence after the fact. Superstition has it that once you lose the key -- your love is locked together forever.

Jennifer was a very knowledgeable guide and we enjoyed her tour…read more Can't say the same for the reception we received at the mansion front desk.

We had a great tour guide who took her time and answered all our questions. The mansion is very…read morebeautiful and the stories were great. Really enjoyed our time there!

My tour guide was Dugan and he was funny, knowledgeable and a delight to spend an hour with. He has…read morea Maine humor routine that is really special, and did some extra things that I don't believe other tour guides would offer. You can tell he really loves what he does! I found the tour operators and Captain to be friendly, professional and have a focus on safety. I heard them say that the captain has a US coast guard Masters license. Maine Duck Tours is a great way to not only see some of the key highlights of Portland, but also spend time in Casco Bay. It is the only tour company in the city that offers this variety. It's perfect for people of all ages, but particularly for groups that are intergenerational or for families. And, if you are really into history, you will love Dugan. He knows his stuff! I recommend it!

The cruise looked promising and the captain and crew were very nice…read more Unfortunately, the boat broke down at sea and we barely made it back to land. We did not finish the tour. The company ordered water taxis to get us back to within a couple of blocks from where we started. No compensation was offered.

Awesome tour! My wife and I attended the Seafood Tour in Portland with Pete and we had a fantastic…read moretime! We went to Andy's, Gilbert's, Rigby Yard and finished with some sweet treats to wrap up the tour. Pete had such a knowledge and love for Maine that we wanted to hang out with him after! I highly recommend the trip and doing it early in your trip any extended stay in Portland - we added a long list of ToDo's that Pete recommended and have not been disappointed by a single one. Highly recommend. Thank you, Pete M!

We had a wonderful experience with our guide, Chuck, on the tour. Chuck was full of interesting…read moreinformation and made the tour enjoyable for everyone. It was rainy, but the balance of inside and outside was good. All of the stops provided delicious food. Would recommend this tour!