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Medway, MA

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Oakland Park

4.7 (3 reviews)

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Choate Park

Choate Park

5.0(5 reviews)
1.9 mi

We were on our way to a picnic dinner at Sweat Beach in Wrentham, MA but they decided to close two…read morehours early and shuffled everyone off. So we googled picnic areas nearby and put our GPS to Medway, MA. The rood trip was winding picturesque road through towns with beautiful houses and finally came to Choate Park. Free and plenty of parking. It's a trash free park, what you bring in, take out. There is an event pavilion and beautiful lake for catch & release fishing ....or turtles ( see pics) lol. There is a fantastic playground for the little & big ones. The trail around the lake has exercise spots and open fields with a huge wall mural. This will definitely be a go to spot for picnics, walking and being in nature.

I took my 5yo and 7yo to the playground and splash area. Very nice park. The splash area is simple…read more(just some fountains that shoot up from the ground) but is great to cool off on a hot day. The water stops at 5pm. I don't think the water area is particularly slippery but i would suggest water shoes. My son and a couple of other children who were barefoot did slip. The playground structures are really unique and fun. They have a smaller one for young kids and larger structure for older kids. There was also a trail and lake but we didn't follow. Highlights: -fenced in with only two doors -bathrooms (clean and open until 5pm) -clean - picnic area with tables and benches. Covered and large with plenty of seating. -electric car charging station (not free) -plenty of parking Cons -no trash cans. Small inconvenience. Overall would def recommend as a summertime activity.

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Choate Park
Choate Park
Choate Park

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Upper Charles River Trail

Upper Charles River Trail

4.0(6 reviews)
5.8 mi

Great place to walk, run or ride your bike…read more It's not lit up at night, so avoid the trail when it gets dark. The people are usually very friendly that you come across, many walking their dogs and surprisingly picking up after their pets. I wish the geese weren't doing their mess on parts of the trail because sometimes if you're running and not looking down- you can step in it. They have tables to eat lunch. People fish there as well. There's also markers so you know how much you've walked or ran. Great trail to see some nature too. We've seen little bunnies, chipmunks, and at one point at dusk I was being chased by a bat. lol So yeah, don't walk there at night. Also the police will check it out from time to time so at least you know they're looking out for you as well.

I first found out about this path when my boss took me here after work one day. He likes to go on…read morewalks to delay returning home when his psychotic girlfriend (according to him) or her psychotic 10yr old daughter (also, according to him) are too much to handle. Sometimes his goal is to wait for them to fall asleep, then go home. I duck out before it gets to that point. The Upper Charles River Trail will eventually be 24 miles long and through Milford, Ashland, Sherborn, Holliston, and Hopkinton. It's on an old CSX right of way. I believe the Milford section is the only section complete so far, roughly ~5 miles. I don't jog that long anyway, especially with the sunset getting earlier. I usually park at Fino Field and go the trail until it intersects Route 85 by the Sports Authority, then turn back. Round trip is ~4.5 miles GPSed. The trail is paved and has mile markers in 1/4 mile increments. Traffic is pretty light when I'm there; dusk, weekdays. I see more walkers and less bikers. There are unimproved trails through the woods that you can stumble into and I'm still exploring where they all go. Also, I believe what they call "Vietnam" has an entrance on the north end of the trail across US495. NEMBA actually owns it. (http://www.nemba.org/Articles/VietnamFAQs.html) I'd like to try Vietnam out, but reading reviews saying that there are "6 foot drops out of nowhere" kind of scares me.

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Upper Charles River Trail
Upper Charles River Trail
Upper Charles River Trail - Upper Charles trail in the winter

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Upper Charles trail in the winter

Ashland State Park

Ashland State Park

4.2(29 reviews)
6.9 mi

Of all the state parks in the area, Ashland has always been my favorite. It's not human-made and…read morehas great nooks and crannies that are fun to explore from a kayak or canoe on the water or along the perimeter on trails. We've been coming here since we moved to the area 25 years ago and because the entire reservoir is within the park property, it looks much the same as it did a quarter century ago. This morning I met a friend and we took our dogs for a walk. We were shocked that on a summer morning, we only passed two people along the trail- one with a dog (on leash as required) and one friendly solo human. The trails are very rooted and while I've done mountain biking here in the past, it's definitely easier to maneuver this one on foot. The trails are *sort of* marked with yellow spray paint on trees. As other people have mentioned, despite many times walking here I still always question if I'm going the right way. Even in the trail area, it's easy to wander off a bit. But also as someone mentioned, the beauty of this trail is that as long as you keep the reservoir on the same side and within view, you'll be fine! I like to park at the Boat Launch side of the park because you can access the trail right there without walking through a giant parking lot- so it feels more natural. I also like to head to the right (facing the water at the boat launch), therefore keeping the reservoir on my left the whole time. The public beach area (no lifeguards) is about halfway from the boat launch which is a great water/snack/bathroom break. The ranger station was open and the bathrooms were, as well. This section of the park has tons of shaded picnic areas and plenty of sandy and grassy space to spread out. This area used to get very busy on weekends with large gatherings - I'm not sure if that's still the case. But today there was one family group having a quiet picnic but the beach was empty. The trail around the reservoir is almost completely shaded except for the elevated causeway across the dam which is about .3miles of exposed trail- also of note are the annoying bugs that zip around this tall grass but seem to not bother humans. Ashland State Park is a great place to visit! Definitely recommend checking out this gem!

I really enjoy visiting Ashland State Park. Unfortunately, the reservoir is currently not safe for…read moreswimming due to bacterial exceedance (otherwise, this park is 5 stars). Without the option to swim, the beach doesn't have the same appeal, but it is still a nice spot for walking or boating. The trail around the reservoir is an almost 4 mile loop, and the vast majority of it is shaded. There are many roots along the trail, and the terrain slopes toward the water, so it is not flat. Just something to keep in mind for folks with knee or ankle issues. During our most recent visit, the trail was not crowded, and thankfully was very clean with very little noticeable litter. We did encounter a small amount of broken glass and a few dog owners who ignored the "dogs must be leashed" signs. Either from the trail or water, the view in almost all directions is natural woods. There are just a few homes within site from the trail, so it really feels like an escape hidden within the suburbs.

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Ashland State Park
Ashland State Park
Ashland State Park

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Hunnewell Park - The Castle/ City Hall in the back. The War Memorial in front dedicated to the Armed Forces @  Hunnewell Park in Wellesley MA.

Hunnewell Park

3.0(2 reviews)
11.4 mi

AN ABSOLUTELY MUST DO! 5 STARS! How would you like to picnic on the grounds of a Castle for FREE!…read moreThis is one of the Secret Hidden Gems of America that most people have never heard of or been to before. It's Time to jump into The TimeMobile & scour the Earth & take you to places from a different time that you won't believe still exist. We have set the dial to 1880's in the town of Wellesley MA. We have landed at this beautiful Castle that is in the middle of the center of Wellesley's business district. Well it looks like a castle but it's really Wellesley City Hall. I don't know about you but my city hall looks nothing like a Castle. LOL! Wellesley is a very affluent town & their city hall is a Castle. You can visit the park here for FREE & THE Parking is FREE as well. If they run out of spots there's metered parking on the perimeter & adjacent streets too. Near the front entrance there is a War Memorial dedicated to those who lost their lives in the Armed Services. The grounds of Hunnewell Park are filled with green grass, trees, a stream, a bridge & a pond. There's wildlife that resides here including white swans & geese. There are benches & picnic tables scattered throughout the property. What a picturesque & relaxing setting to Picnic or kick back & read. It feels like you are at a nature retreat rather than a park. It's great to take a photo here with the Castle & send it to your family & friends & say " Sorry I can't talk to you peasants now, I'm picnicking at a Castle". LOL! They will hate you forever until you tell them it's Free & you'll take them with you next time. The stone government building is a prime example of the Richardsonian Romanesque style of architecture along with a bit of French Chateau. It was built between 1881 & 1886 & designed by Shaw & Hunnewell. It was funded by & built on donated land by H. H. Hunnewell. The building is now listed on the National Register of Historic Places. There's also something special here for the medical community that they will really like. There are 2 Doctor memorial plaques placed on large stones. The first one is for DR W*T G MORTON who lived here. He gave the world Ether for Surgery. The second plaque is for DR. JOSEPH E. MURRAY who in 1954 performed the first successful Human Organ Transplant. He was also a 1990 Nobel Prize Winner & resided in the town. Since you are in the area be sure to check out the Babson Globe another Freebie. It's the 2nd largest rotating globe in the world. And you can get something great to eat right across the street @ Tutto Italiano. They serve great Meatball Subs & get a side of their Delicious Homemade red roasted peppers too. They also have authentic Italian red sauce to go. It used to be, you had to have Mega Bucks & be really Rich to have the Good Life, not anymore. The Game has changed. You've been Upgraded. Now You Can Live Like a King on a Limited Budget!

I spend a lot of time at Hunnewell Park. It is close to my home and although it used to offer a…read morelot more natural settings it has unfortunately become one giant athletic complex. Lights and sounds can be experienced almost every night now. We used to see and hear many more wild animals and experience it as a natural corridor. Alas, now it is only filled up with athletic equipment, stray plastic water bottles and other human trash.

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Hunnewell Park - Free picturesque relaxing park perfect for picnicking  with a Castle, green grass, trees, a stream, bridge & pond @ Hunnewell Park.

Free picturesque relaxing park perfect for picnicking with a Castle, green grass, trees, a stream, bridge & pond @ Hunnewell Park.

Hunnewell Park - The Town Hall Bell. The 1880's stone structure in a Richardsonian Romanesque Architectural Style is a Castle/City Hall.

The Town Hall Bell. The 1880's stone structure in a Richardsonian Romanesque Architectural Style is a Castle/City Hall.

Hunnewell Park - The beautiful historic 1880's Richardsonian Romanesque Architectural Style looks like a castle but is City Hall @ Hunnewell Park Wellesley

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The beautiful historic 1880's Richardsonian Romanesque Architectural Style looks like a castle but is City Hall @ Hunnewell Park Wellesley

Oakland Park - parks - Updated October 2026

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