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.

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.

Locals said this is the most photographed and most painted lighthouse in the world! I think it's…read morealso the most beautiful! It's fairly easy to get to, and parking is easy as well. There are easy trails all around the lighthouse so you can walk to different directions and take photos from different angles. On a clear day it is beautiful beyond words. Though not that easy to get to, Portland is a beautiful town, worth a serious visit. This lighthouse just makes it so much more spectacular!!

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.

The fort overlooks some nice looking water. The park itself offers a small amount of parking, no…read morefacilities of note, and a bit of a historical exhibition. There are stairs leading down to the waterfront. This spot is nice for the aesthetics, but will be a brief stop for most.

"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.

**November 2025: Friday Morning Visit**…read more I saw that the Victoria Mansion was just a 10 minute walk from our airbnb and that Black Friday was the start of their Christmas overlay! It sounded fun and for $19.25 (Adult Admission) I was excited to see how they would implement the Nutcracker theme to the home. Guests enter through the gift shop and while we arrived at 10:10am or so I was really surprised at how many visitors they had checking out the home. As a National Historic Landmark, this summer home was created by Ruggles Morses, sometime between 1858-1860, and as a hotel entrepreneur Morses implemented many of the lavish hotel designs to it. The home itself is original and over 90% of the interiors and furnishings remain original to 1860, including furniture, carpets, draperies, textiles, which was really impressive. I think I spent about 45 minutes admiring all the home details and reading the placards, and there were friendly informative docents at pretty much each section of the home These photos don't even really do it justice, but the decorations were extremely elaborate and each room focused on a different act in the ballet - ie. Spanish Chocolates, Mother Ginger, Arabian Coffee, Chinese Tea, etc. There was significant care given to each room. Overall, I had fun time!

Street parking was relatively easy for us. No paid meters, but read the signs. $38.50 for 2 adults…read moreis what we paid. That price came with a guided tour of the house and narration. Our guide was actually doing a very good job narrating, that is until she seemed annoyed that we wanted to pose for one or two pictures, hurrying us along and stating we were waisting time. Even the grand staircase, not allowing us to stand in the middle of the steps for a photograph. Telling us that wasn't allowed, it all sounded ridiculous. I mean it was just two people the guide was touring, us! The guide even walked us past the tip box we weren't tossing in anything. Great post card photo opportunities in house, which are allowed. *Videos prohibited. *Final thoughts: Nice and interesting experience go check it out and tell them the Guru sent you. Check out the documentary OLD WORLD ORDER 1&2 at rumble dot com before visiting. The Review Guru* Long Island NY

Tour was ok, but a little boring for the kids - lots of "dad, can we please get off soon?"…read more We booked for an easy tour, but in retrospect would definitely go with a smaller boat and more unique tour. Would probably be 2-3 stars, but bumped further down to 1 for the very rude tour guide.

Fun time!! Our 1st time in Portland and we decided to take a tour of the city and harbor. If you've…read moreever done the Duck tours in Boston then you know you're in for a treat with Quack N cruise.

We came to Maine very VERY early season (March 20th-24th) and were looking for something to do…read more Most of the area is still in full 'pre season' mode, with many restaurants and services closed, especially during the week. We found the walking Food tour on Viator and jumped at it - and boy were we glad that we did! Because of the time of year, my wife and I were alone on the tour and as such got to spend around 3 hours with our guide, Ray Sapirstein. Putting aside Ray's obvious love for Portland and food in general, he was a charming guy - keeping us engaged and entertained with stories about the area for the entire duration of the tour. Ray is a PHD trained historian and, as such, was able to fill in a lot of color about the area, going beyond the 'food' aspects of the tour, describing the 'hilly roads' which were sand dunes were covered up to build out the city. Add to that the fact that he took us to several places that we NEVER would have found via googling for 'best ofs' and would have been a HUGE failure to miss! Andy's Old Port Pub - a neighborhood bar (don't call it a dive, though in my mind it qualifies). Spend some time chatting with Thomas, the owner, and Steve the bartender - and had what I can only describe as the single best haddock taco I've ever had in my life. Do not judge a book by it's cover: this place is AWESOME. Great craft beer tap list, and a warm and friendly environment. If I lived in the area, this would be my regular. From there we went to Gilbert's Chowder house right next door - Ray was again right: don't sleep on the seafood chili - it was RIDICULOUSLY amazing. After that we paid a visit to the Harbor Fish Market where we got to see the recent catches, and as Ray pointed out the 'transparency' of the thing: fish are cleaned and prepped for sale right where the customer can watch, and all fish are labeled as 'fresh' (with VERY few pre-frozen exceptions). This is also the place to go if you want to buy Maine swag. From there we proceeded to Rigby House, an unassuming 'coffee shop and workspace' that Ray promised us had nothing short of the best lobster roll in Maine: I've had some good lobster rolls so I can't quite commit to that, but the bread it was built on was FANTASTIC, baked locally from one of the bakeries rated tops in the nation right in Portland. This stop came with either 2 samplers or 1 full pour from their 20+ menu. Don't miss the blueberry ale. It's a rare treat and again, came from Ray's love of his city. From there, we visited Dean's Sweet shop for a couple of truffles and terrible jokes, and then Fiasco's Gelato to round up our day - try the lobster gelato, it's weird and not something I'd necessarily do again...but glad to have had the experience. The whoopie pie gelato was top notch and the blueberry was one of the best gelatos I've ever had. For a 3 hour tour, with all food included, we were certainly full and happy. The walk was short - I don't think we wandered more than a mile in total - and when we were showing signs of being "Help me I'm not from Maine cold", Ray took us into Grittys, another neighborhood bar just for a warm up.

I attended the Portland: Old Port Culinary Walking Tour on Sunday, June 14, 2026 at 10:30 am with…read moreAnne and Ross. Usually, there is only one tour guide and it was supposed to be Anne only but Ross joined in as well. The Old Port Culinary Walking Tour is a foodie tour with a mix of history and culture. Our group consisted of 13 people. The tour starts at Andy's Old Port Pub with an introduction from our tour guides. At Andy's Old Port Pub, we were seated in the backroom and had a seasoned, grilled fresh haddock with house-made pickled vegetables, pico de gallo and lime crema in a corn tortilla and Andy's house Lager. Ross talked about the suspicious happenings and history at Andy's Old Port Pub. They both talked about Harbor Fish Market which was right across the street and how the seafood never see the back of a truck. I thought the fish taco was okay and was probably my least favorite food item from the whole tour. Andy's house Lager was very smooth and I really enjoyed it. Then, we walked next door to Gilberts Chowder House where we had a choice of Clam Chowder, Haddock Chowder, Corn & Chicken Chowder, Seafood Chowder, or Seafood Chili. I chose the Clam Chowder. The Clam Chowder was thick and not as creamy as I usually like my clam chowders. Here, Anne was showing us pictures of lobster abnormalities. After having our chowder, we walked to the historic U.S. Custom House and old fishing docks. We even got a postcard of the old fishing docks which was a nice souvenir. Next, we stopped at Rigby Yard and were seated in a small private room. We were offered several drink options; I chose a glass of prosecco. We had the Fresh Maine Lobster Roll with fresh Maine lobster meat Maine-style, tossed lightly in mayo, lemon, and sea salt served on a brioche roll with chips. The lobster was definitely fresh and good. The last two stops were dessert spots: Dean's Sweets and The Gelato Fiasco. We had a needham which is a confectionery dessert bar made from sugar, chocolate, coconut, and potato and we had the option to choose another truffle. I chose a blueberry one. At The Gelato Fiasco, we were able to choose 2 different flavors. Funny enough, I had went to The Gelato Fiasco the night before and it really is delicious gelato. I was glad to try different flavors. The tour finished about 1:45pm. The tour guides thanked us for spending our time together. The Portland: Old Port Culinary Walking Tour was fun and I enjoyed meeting the other people in our group. Anne and Ross were very knowledgeable with Portland's history and food scene. They had good recommendations for other things to do in Portland. The food we had on the tour was okay according to my opinion, but it was definitely a good variety of Maine dishes.