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Sheepfold Park - Middlesex Fells Reservation


Category: Cruisy park , trails Hours / Entry Fee: Open morning till dusk Directions: From I-93 take Exit 33 and head up Fellsway West for about one mile. The entrance will be on your left.
Submitted: Oct 29 2002 (Edited 11/29/17)
Cruised here? Rate this place:
2.51/5 based on 69 votes. The median rating is 1.
Read & Write Reviews: 34 Reviews

Address: off Fellsway West
City: Stoneham
State: Massachusetts
ZIP/Postal Code: 02180
Country: United States of America


GPS Approximate Latitude & Longitude: 42.4526,-71.1059
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Older Reviews : Show/Hide
Thomas Mac Donald

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Posted Nov 26 2021:
Heads Up!
It was on the news tonight that a woman was sexually assaulted in the Winchester section. Steer clear for now.

Edited on 11/28/21
Dan

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Posted Nov 27 2017:
Heads Up!
Squirt took down their page for Sheepfold so something has gone down in the past year. I haven't been there in a while but the last couple of times I was there, there was always a DCR truck in the lower lot and sometimes a state SUV would pull in and out.

Just don't do it out in the open. I recall one incident where a yuppie couple on bicycles almost caught a couple guys who had been fooling around on the path going up to top of the center hill. One of them was wearing a camera on their helmet. A close call.

Edited on 11/29/17
Tylercamerin80
Reviewer

Usergroup: Member
Joined: Aug 30, 2015

Total Listings: 0
Total Reviews: 1

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Posted Aug 30 2015:
Heads Up!
This place is amazing! There are guys with big dicks showing off. Most guys are totally nude.

Lately there is a larger police presence in the morning. I would stay away from the area until they go away.

Edited on 09/04/15
bisunbather

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1 of 1 people found this review helpful
Posted Apr 16 2012:
Heads Up!
Was at Sheepfold this past Thursday and two rangers were on foot, searching the area, both the front hill and the area out back on the rocks where guys sometimes sunbath. I'm not sure if they're allowed to write tickets, but they were acting very aggressively.

Edited on 04/22/12
Old Timer

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1 of 1 people found this review helpful
Posted Sep 18 2011:
Guys go to the right of the old rail bed trail as you walk into the woods to the north, and the further you go, the more private, and the fewer guys. Just before the end of the rail trail there is action on both sides, up on the hills. During the week the average age is 60+, but on weekends, you get a real mix of ages. A few psycho's, too. My favorite is the 40+ guy who lies out naked and JO's his sizable dick, and if you watch it, and are not hot enough for him, accuses you of stalking him, and threatens to report you to the cops.

Edited on 09/21/11
Tim

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Posted Jul 27 2010:
I come here all the time. It gets very busy around 1 pm. Just park in the first parking lot on the right and if you walk the trails that run parallel to 93, you will find some action. Myself, I've had some hot orgies up there.

Edited on 07/29/10

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1 of 1 people found this review helpful
Posted Nov 04 2009:
I went there twice in a two week period and each time all I found was old, fat, hairy men.

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Posted Jun 08 2009:
This place is 50-50. Either 50+ years old or 50+ inch waist lines.

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Posted May 09 2009:
Saw nothing but trolls and old guys who'd seen better days. Am I missing something at this place?

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Posted Mar 03 2009:
I was there last Friday and got sucked by a very submissive man. Lots of guys were there and it was nice and sunny.

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Posted Mar 01 2009:
I'm looking forward to the cruisy season. It usually starts in May (I know, a couple of months) but as soon as there are warm days in March the cocks will start flying.

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Posted Nov 23 2008:
The dog park people know full well that guys cruise in the back of the Sheepfold park. I met a couple who were trying to organize hikes through that area to try to 'take back the park.' Expect more foot traffic from straights. Be discreet and keep off the trails and out of sight if you're hooking up. I've seen guys whip it out in plain sight on main trails and also the trash up on the hilltops is horrible -- coffee cups, used rubbers and paper napkins everywhere. It would be sad to see a great place like this ruined by a few idiots.

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Posted Sep 17 2008:
I went there last weekend and blew a guy with a great cock, then found another Brazilian guy that I fucked in the woods. There are a lot of guys here, especially when getting out of work.

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Posted Aug 09 2008:
This place is dead because everyone is in Provincetown this summer.

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Posted May 16 2008:
I went the last couple of weekends and had a good time. Now that it's warmer the action will pick up. Had an amazing group blowjob and ass-fuck the first weekend. The second weekend I got fucked on a side trail by a hot black guy with an enormous cock. Let's hope the action stays consistent through the summer.

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Posted May 08 2008:
Action here is good. Springtime brings lots of dog walkers and bird watchers. Keep your eyes open. Go to the hill in the back on the left of the main trail. There's nude sunbathing, lots of good sex and good-looking guys. Many trolls too. Be careful out there.

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Posted Sep 26 2007:
When you enter the Sheepfolds Reservation stay on your right and take the first parking lot on the right side. The other parking lot is for dogwalkers and families. This place always has a crowd coming and going so I'm surprised people can't hookup. I wouldn't suggest meeting and screwing in the woods but there seem to be enough married guys who want to go back to their place and have some fun.

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Posted Aug 12 2007:
I went today and saw two parking lots, lots of dog walkers, a few bikers and no action anywhere. Specific directions would help a lot.

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Posted Aug 05 2007:
Great spot! One comment: litter is everywhere. If you don't want this place closed I suggest some of you regulars take a plastic bag and a backpack and start cleaning up the litter. It is things like this that close a place down fast.

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Posted Jul 06 2007:
There have been additional police in this park but there have also been additional guys treating this like a red-light district and generally acting stupid. If you hookup, take your trick far off the main trails and make an effort to pick up your rubbers and cum rags.

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Posted Jun 18 2007:
Heads Up!
Major police presence here yesterday, the 17th.

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Posted Mar 25 2007:
Had my ass filled with cock the other day -- it was very warm out. Bent over and took it up the ass and motioned a guy watching to come over so I could suck him off. It was very hot.

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Posted Dec 23 2006:
Busy here year-round as long as there is no heavy snowfall. Wide age range. It can be very hot.

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Posted Oct 11 2006:
This place is always buzzing with both old and young. Met a couple of guys at different times and went back to their house. A lot of married guys come and go. You don't even have to park in there to meet up with some guys...great spot, especially in the afternoon.

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Posted Apr 10 2006:
Now that the weather is warming up the action is starting to pick up here. Go all the way back into the park for the hottest sex.

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Posted Oct 04 2005:
Cops do come through the lots and will sometimes park in the little lot used mostly by cruisers. They rarely get out of their cruiser. I've even driven in and parked while one was sitting right there. As long as you look the part (hiking clothes, bottle of water, etc) nobody blinks an eye. It's the stupid old trolls in the suits and ties who walk through here hoping to get some head that will ruin it for everyone else. If everyone is a bit more discreet, this place won't get busted and shut down.

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Posted Aug 05 2005:
Cops don't ever get out of their cruisers so if you park in the main lot and walk back to the cruisy areas you should be fine. I've rarely left without getting any here. Of course it's much better in warm weather. Weekends are busier than weekdays and the crowd is much better looking. If both lots are full you can park on the opposite end of the park right off the highway exit (the Winchester Highlands exit off I-93 southbound). Then the best cruising is just a short walk through the woods behind the lumberyard.

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Posted Apr 14 2005:
Heads Up!
I was here today. The State Police were checking the ID's of most of the cars when they were leaving lot. Guys leaving woods in droves indicated a couple of cops spotted a couple of guys, and that they were blocking the exit to catch them. Be careful.

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Posted Mar 27 2005:
I went this afternoon, and came across two separate pairs of jocks going at it. One of them was half naked with a face of cum and a big smile. I gave a blowjob to a hot Latin guy, and got a hot hand job myself.

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Posted Nov 07 2004:
This place definitely is a hot spot in good weather. Even off-season, there's a contingent of cruisers in the parking lot looking to score. The warm weather action is pretty hot. The guys are a good mix. You can find anything you're into: young, old, masculine, feminine, chubby, or hot. I have sunbathed nude here, and have seen and hooked up with others doing the same. The action seems to stay closer to the parking lot in colder weather, and in warmer weather stretches out to the very back of the park. I've seen unsuspecting straight couples walking into the cruisy areas with their dogs. Just be smart about it and you can have a great time here.

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Posted Jul 26 2004:
I got my butt plowed good in a secluded area here. There were hot guys on the weekend I took multiple loads. Awesome!

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Posted Jul 10 2004:
There are some hotties at lunchtime, but it's mostly old guys in the afternoon. I got a handjob from a cute Asian guy.

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Posted Mar 01 2004:
I went here yesterday and it is obvious that the warm weather was making the natives restless. The place was crawling with all sorts of guys, from hunks to grampies and chubs. The main cruisy spot seemed to be way out, back across the second bridge up on the hill to the left. I saw a bunch of guys there. One was naked and jacking off behind a boulder, another jock type came along and just whipped it out for me in all of it's eight-inch glory. I sucked off one guy and got sucked by another guy before I finally let it spew. The parking lot was totally crammed with families and dog walkers. I parked along the street by the Marjam building supply warehouse and walked up into the main cruisy area from the ‘back door'. This is right at the Winchester Highlands/Melrose exit on I-93. Believe it or not, this is actually less of a hike to the cruisiest areas than parking in the main parking lot. Just follow the trail. It's easy to spot from all the damn mud. Stay away from the first hill nearest the small parking lot. There are a bunch of guys there but I saw an MDC ranger walk through. He snooped around a bit then turned around and went back along the edge of the woods near the go-cart hill.

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Posted Sep 29 2002:
The parking lot is locked after dark. You must get out of your car and obey the signs (head in parking and no live parking). The cops will ticket/tow. Follow the paths to old railroad tracks (no tracks now) and basically follow 93n. The entire woods a very cruisy. Just follow the paths. Weekends are a little more dangerous due to families. The MDC do periodically patrol and there have been arrests this year. If you are discreet and careful it can be a lot of fun. Best times to go are noon-ish and after work until 8 pm.
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