Where to Picnic in Weston

Picnic tables and tree stumps at Wellington Farm

Spring has sprung and picnic season is upon us. Pack up your melamine plates, red-and-white checked napkins and tablecloth, and head outside. If you’re tired of hanging around in your own sports-court and nitrogened turf backyard, come and check out some of these other places.

  • Town Green. It’s pretty hard to compete with the Town Green in picnic-ability (it’s a word). Beautiful wide open green space surrounded by tall trees, a playground next to the Town Hall, First Parish Church bells on the hour, and of course the occasional loud bangings of Town Center construction. You can pick up your picnic at local places Bros, Dumpling Daughter or Ye Olde Cottage. Or bring it from home, you choose. At least two picnic tables have been seen around the location, somehow they seem to migrate so tie one down and sit down. Or spread your own blanket on the ground and enjoy the sunlight. Parking all along Town Green.
Sit here.
  • High School. The Owl is somewhat reluctant to advertise this one because it’s a pretty good secret. There’s a beautiful little pond, some tennis courts where you can watch people be more active than you are, and a few seating choices including picnic tables and benches. Lovely trees, plenty of places to walk. Please be aware that the campus is not open during school hours and that field priority is to the students. Parking outside of school hours is at the parking lot near the basketball court and turf field. 444 Wellesley Street.
Rope swing!
  • Wellington Farm. This spot is another well-kept secret. You’ll need to park at the entrance to Norumbega Reservoir, walk a short grassy trail (no dogs, this is MWRA land) and then head down another trail into Conservation land. A small rise leads to tree stumps in a circle and a picnic table (and…bonus.. a rope swing). You’re hidden in the trees so don’t count on this one for vistas. You need to carry in and carry out. Please don’t leave any trace. Wellington is just south of the Mass Pike and north of Glen Road. Park near the entrance to Norumbega Reservoir.
Pre-Covid photo by Land’s Sake
  • Land’s Sake. This one is not at all a secret, and set up for success with lots of picnic tables, historic trees, and if you’re lucky, the farmstand will be open and you can add some tomatoes to your picnic. Oh, okay, so that will be in say, August but plan ahead. The bunnies are back and it turns out they were NOT brothers so they have a little bunny kid. Chickens are also around being chicken-y. Take a stroll around the wide-open fields but don’t crush the agriculture. Right now the trees are in full bloom and construction has not started–park in the gravel lot at 90 Wellesley Street.
Stone benches and large trees. Perfect
  • Legacy Trail. Here’s another place that’s hard to beat in terms of a nice walk, sunlight, a fine sunset hour and a view of the Case buildings whose futures are in doubt. Oops, editorial comment. You won’t find picnic tables here but there’s always space on a big granite bench. Take a side tour of the Ash Street connector, the Ash Street Reservoir or the Outdoor Classroom. Please park in the lot near the Recreation Center and walk-up. Please also carry in, carry out and all dogs must be leashed at all times on Case Estates.

Now if you’re okay with an old-style picnic, which in the Owl’s memories of childhood figured as a trek up a hill with some hard-boiled eggs and some cheddar cheese and a seat on the rocks with a view of the Hudson River, then there are some other recommendations. No Hudson, though. No picnic table either

Far in the distance is Boston.

Doublet Hill viewpoint. Where else can you get a view of Boston without walking more than a quarter-mile of your car? Well, Route 2 near Lexington but then you’ll be eating and driving. A short walk thought the forest, and up a rocky outcropping and you can see Boston’s skyline through the trees. Spread out that picnic blanket, open the hearty burgundy (just kidding– you can’t do that on town property, oh and not sure hearty burgundy still exists) and enjoy the woods. Take a hike–the lovely Hemlock Pond is just downhill from the viewpoint. Parking is at Doublet Hill trail head (very limited–four cars only–please do not annoy the neighbors by parking illegally on this private road). Pack in, pack out.

Cat Rock Park overlook. Ah, Cat Rock. Well, at the top of the old ski hill, there’s not as much “eau de dog poo” so it can be a nice place to hang out and see the skyline of… Waltham…and imagine the good old days of rope pulleys and no lawsuits when you ski into trees. There might still be a bench up there; one was stolen (seriously must we repeat the take only photos, leave only footprints and never ever dog poo line, so boring). Park at Drabbington parking lot (residents only on weekend) and take a stroll up the hill.

Orchard views at College Pond

College Pond/Burchard Park. One of the best days out you’ll have in Weston. Watch a Little League game at Burchard, or have some batting practice yourself. Wander the trail around the pond to the other side where you will find two huge stone outcroppings just made for sitting on. Prefer an orchard view? Head up the hillside to old apple orchard–in the fall you can even find some misshapen, sour and delicious apples. Hike, play, picnic. No tables. Okay, one by the snack shack, maybe two. Burchard Park has plenty of parking. 269 Concord Road.


If you have another favorite spot, tell the Owl. Or don’t. Keep it to yourself–your own magical spot. The Owl may or may not have done the same.


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