Winning Farm - Wicked Wierd

Imagine wandering out of an upscale Boston suburban neighborhood of million-dollar houses into a nightmarish overgrown tangle of abandoned, collapsing houses, trailers, pieces of long-forgotten amusement park equipment with twenty-foot trees growing up through them, moldering picnic tables, and the remains of a show horse arena ... and you can begin to understand the strange feeling of entering the back side of Winning Farm from an obscure trail off Blueberry Lane in Lexington. I'd love to know more of this area's history. Trails from the clearings of Winning Farm disappear into the Winchester forest, and someday I'll explore them further, past the piles of abandoned lamp posts resting near the gas line clearing...

Check out the Google satellite view of this bizarre area on the Lexingtion/Winchester/Woburn town lines. The satellite image shows the tops of the abandoned houses, but you've got to be there on the ground alone (maybe on a moonlit midnight?) to appreciate it. This place has truly been abandoned (but occasionally mowed, it appears) for years, but not for much longer... Development is on the way! Enjoy its desolate charm while you still can, if you dare...

Somewhere within this area is one of the missing links of the Lexington Loop Trail. It may be able to become "found" with the right combination of events... If Lexington acquires the 8 or so acres of Winning Farm land inside the town borders, if the planned assisted living development of the Woburn part of the Winning Farm land allows access from Lexington over to Woburn/Lexington street, or perhaps if a connection from the 8-acre tract to the roads of the condo complex on the Lexington/Woburn line is arranged....

What is this missing link? It is indicated in green in the small map, which is a section of the larger Lexington Loop map. It is a link between Whipple Hill (the highest point in Lexington) and the Shaker Glen conservation land entrance at the end of Rolfe Road. Without the missing link, a nature-loving traveler from the small Whipple Hill parking lot on Winchester Drive (Johnson Rd. in Winchester) would have to follow Winchester Drive 0.7 mile down the long hill, turn right at the stoplight onto Lowell street, follow Lowell 0.4 mile to the light at Woburn Street (a busy stretch indeed), turn right onto Woburn, then left across traffic into Rolfe and a little peace and quiet...

With the "missing link" in place, the traveler coming from Whipple Hill can travel just 0.15 mile on Winchester Dr., then duck right to quiet on Tyler Road, right again on Blueberry Lane, and head into the Winning Farm forest to the right, near the middle of Blueberry Lane (0.35 mile from Winchester Dr.). After emerging from the forest onto Woburn St. close to the Lexington/Woburn line, our traveler will only need to cross Woburn St. and head left along maybe 0.05 mile of sidewalk before again leaving the bustle of traffic by turning right into Marshall Road, left on Fessenden, and finally right on Rolfe to find Shaker Glen.

The missing link avoids nearly a mile of busy roads with two traffic lights. It ties the Shaker Glen neighborhoods to the glorious Whipple Hill heights along walkable, friendly trails and sidewalks. What's not to like?