Deering Oaks, a 55 acre park in Portland, was created in 1879 by then City Engineer William Goodwin…read more(DYK: the park didn't have lighting for almost a century!). His hope was that "The Oaks" would be "a public breathing space". Over the years, the park has evolved - in 1883 the bandstand was built, in 1887 the duck house and fountain were installed, in 1894 the Castle was built (as a hut for ice skaters to warm themselves), and in 1902 a playground was built. Fast forward to current age and Deering Oaks is the home to farmers' markets, the Festival of Nations, performances of all kinds, Twilight in the Park, and a whole host of other amazing events. We've truly done an excellent job at making it a unique-to-Portland area where people truly can decompress and enjoy nature (I almost touched a squirrel here once, but he realized I had no snacks and quickly lost interest; next time... next time...; it was also the home to our rare great black hawk for a spell). Yes, there parts of the park that might be "a little rough", but all in all it's BEAUTIFUL. Spring and summer brings on a million shades of green and wee ones playing in the wading pool; autumn is positively ablaze with orange and red hues; and during winter you'll see the tree with long arms covered in lights, along with hockey and ice skating on the pond! For me, it's one of the best representations of the seasons that Portland has. Here's my suggestion to you: if you see there's trash in the park, be a good citizen, and pick it up. Let's continue to make it the space that Wiliiam Goodwin had planned for us 'lo those many years ago!

Duck poop all over lol watch where walk on the pathways. Free parking by the entrance by ranger…read morestation.

I love the views! It's great for a picnic and a little bit…read moreof history. There's plenty of open space for you to hang out with family or friends and enjoy the ocean views and breeze. While it may be controversial, I'm glad they moved the food trucks to the lower lot. It's less crowded when you arrive and less crowded near the food trucks - meaning only people getting food are in the area, vs people walking/running through with animals and kids that aren't going to the food trucks. It's also less noisy not being next to the generators. We love the food trucks there and will continue to enjoy them while also enjoying the peaceful hill. The kids in the family really enjoy the canons and the playgrounds. The times we have gone the playgrounds have been clean - thankfully no needles or trash anywhere to be seen.

The Eastern Promenade is a popular place to take a walk in Portland and see the water. There were…read morelots of people so we had to search for parking but it wasn't bad. We walked down to the Portland Paddle area. You can reach the water but there is not a beach there. Some people find a place for a picnic on the grass. Others ride bikes around the Promenade. The views of Casco Bay are good.

One of the most beautiful lighthouses in Maine! I love going and walking on the path and seeing all…read morethe sites! Make sure to see the fort ruins as well, it's very fun!

Im patting myself on the back for booking this trolley and lighthouse tour!…read more Our guide, Wendy, was stellar- knowledgeable- friendly - funny and genuine. She showed us incredible architecture, shoppes, etc. What a doll! Since we were the last tour of the day, we got to stop here. A MAGNIFICENT way to end a lovely trolley ride! The park has stunning views and we loved the lighthouse. We took plenty of photos and enjoyed a sumptuous gelato from a food truck. GOOOOOOOOO HERE !!!!!

The West End is a promenade that's located on the edge of an area called Brahmall Hill and is…read morecurrently listed on the National Register of Historic Places in 1982. It's got beautiful and historical architecture with it's Victorian homes (and, apparently, former sea captain homes as well), stunning views of NH's White Mountains on clear days, spacious green areas and walking paths, a tree swing, the Western Cemetery fraught with our cities deceased wealthier ancestors, great walking areas, and it even once won an award from the Portland Phoenix for having one of the best secret spots to make-out in a tree (I kid you not). To me, the Western Prom is the established, composed, unruffled older sister (who's probably quite proper and likes garden parties) to the Eastern Prom. I'd like to think I've got a little West End in me, and it's fun to pretend I belong there when I'm picnicking and watching the planes come in and out of PWM from a distance. I've seen kiddos practicing lacrosse here with their dad, people relaxed under trees reading, friends playing a pick-up game of bocce while drinking something out of red solo cups. There used to be more events held here (... the legendary Halloween parade is not to be missed); so hopefully those concerts and outings begin to happen again!

Lots of benches and green space, a meandering path with some interesting trees and a few small…read moregardens, and some lovely Victorian houses to look at as you meander. Unfortunately the views aren't that great (unless maybe at sunset) and there isn't a lot of shade seating. A good option if you're already in the area but not a destination park in my mind.

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.

I have noticed this trailhead many times on our trips to Old Orchard, but never had time to stop in…read moreand check it out. Today, we did! I'm so glad! The trail is beautiful, and easy for anyone (except a wheelchair, sorry) I have a bad knee with limited mobility, and this was doable for me! I'm so glad we made it out there today. The waterfall was at full force, and was so gorgeous. The little landing area at the bottom was full of downed trees, but the kids were having so much fun climbing and navigating. There were people flitting about in every which way, miniaturized by the big waterfall. The bridge was washed out, looking to be repaired, so I think one access from the loop was cut off. But people were navigating over the downed trees and on rocks. Nobody seemed to care. It was a blast! HIGHLY recommend this trail.

Free parking and a nice short trail to a cascade. It was dry when we went so the cascade was a…read moreletdown tbh but still a fun time

Jewell falls is a waterfall of water flowing from the Fore River and is named for Tom Jewell who…read morewas one of the founders Portland Trails and very much alive today. Did you know that Portland Trails started in 1991? He donated the land around the falls and the rest of the land the trail walls through is a mix of public and private land. You see evidence of this with many marked signs that designate private property -- good to respect these so we can continue to walk these trails. Somehow I got lost off my usual path I take and ended up going on the greater fore river sanctuary trail loop around and across the railroad tracks, but the boardwalks were great! Back to the falls, if you start at the trailhead near Brighton ave, it's less than 0.25 miles of a walk. The falls are made of horsetails of rushing water over large slabs of rock. The trails are really well maintained and there's not too many people. You can definitely still hear traffic from some parts but there are a few quiet enclaves.

This hike is a nice place to take a short stroll for the locals but not a place I would recommend…read moretourist to come. First off, it is only about half mile from parking to the waterfall. So total hike was only 1 mile. it is a WALK, not hike. Good for families with young ones. Be very aware that the mosquitoes here are super HUNGRY! I have never gotten so many bites within such a short time inside a hike! I got 6-7 bites all over my legs just from hiking here for 30 mins. My husband got 8+ bites all over his body! Luckily my little one only got 1 bite. We were all over Maine in the last 2 weeks including kayaking and out at Acadia national park. All outdoor activities and barely got any bites until now! There are other trails here too but after getting so many bites, we wanted to run away as fast as we could! I wish I didn't come here. View and waterfall are not worth it for trade off of these hungry hungry mosquitoes!! *sooo itchy* :-/ Bring bug spray if you wanna come!

Every time I see this park it looks considerably nicer than it did the time before. It's meant to…read morebe apart mostly for toddlers and grade school children. Although at first I was turned off by the no dogs sign I realized that in Portland with our Somalian community that if dogs are allowed to play in the park Somalian children may not want to or be able to for religious reasons. It's a tiny park not really good for dogs anyway. The first time I saw this park it was midsummer and probably minutes from sunset, it didn't look as nice as it did the next couple times and perhaps it's because it's actually been cleaned up or repainted, or perhaps it's because the rough elements hasn't been seen in any of my following passing by's. I believe now that the neighborhood daycares and/or preschool uses park that parents are getting stricter and the police as well about keeping the drug addict and troublemakers and homeless winos from using the park 4 there less child oriented usages.. The park is at Cumberland and Montgomery and had a to jungle gyms and 10 benches and some grassy areas to sit or play or picnic on. If I was a kid I would give it a 5 star

This is a good park however there is litter everywhere which is disappointing. The equipment is…read morestill in good condition and they even have a little shower for hot days. If a local organization did a clean up day this park would get 4 stars.

Well this is indeed different. It's lovely and the fact that on a hot day it is completely shaded…read morewith 50 to 100 foot tall trees covering every step of the way. I definitely recommend wearing appropriate shoes and clothing especially until you know what kind of plants and wildlife are out here. There are two trails one says it's handicap accessible the other which I took is definitely not and it is not for anyone with any kind of difficulty walking. Cool little creeks let the dogs playing not too deep this time of year maybe 6 inches to a foot in most places. Definitely a good off leash area not too many people here in fact you could go an entire walk without seeing anyone so I'm good for quiet time to think or chat on the phone well you hang out with your favorite canine companion. Maybe was to wear bug spray won't know till tomorrow if I'm covered in mosquito bites but no sound of flies just little tickles here in there.. I was a little worried about getting lost at first but to the road that you can hear the sound of cars although not so close that you have to worry about your dog running into traffic. What I like the most about it is that it's actually a good hike and good exercise and it's different than the other dog parks and it's more a hiking trail that you can bring your dog and allow it off leash then it is an actual dog park. Also make sure you bring your own bags and water if needed. And most of all have fun

This trail is part of the South Portland Land Trust's West End project. The trail head itself is…read morelocated to the right side of the Home Depot parking lot by the stone wall. You will see the kiosk. Part of the trail is paved and you will be able to go around the Home Depot building. There is a short dirt trail that is marked as handicap accessible and only goes a short distance in to the woods and there are benches to sit and look out over the water on either side. You can follow the smaller path down to the water. If you follow the paved trail to the right you will come to the dirt trail that skirts the pond. This is packed dirt and there are stairs and tree roots. The trail is becoming more and more popular. Expect to see people walking dogs here off leash. This trail connects to the Red Brook Trail as well that goes behind Sappi. We have seen many herons, ducks, an owl and what look like fox dens. There are signs of beavers, but we have not seen any. This is a great walk while being on the heart of a busy area of South Portland. Depending on the path you take, this is approximately 2 miles long. *As a side note: there are some "camps" in this area and we have come across some transients and homeless in this area. As always, take safety precautions for trail walking.