This is the southern end of this multi-town trail. The trail starts at the Wedgemere Train Station and heads into Downtown Winchester.

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We returned two days later to walk more of the trail. We picked up where we left off in Downtown Winchester. There are some interesting sculptures right along the trail. At the high school, the trail splits off in two directions. One heads to Woburn and Stoneham, the other goes to Horn Pond. We took the trail to the pond. This section is also known as the "Horn Pond Bike Way". The dedicated bike trail ends in a few places, and the route follows a side street, but this portion also includes sidewalks for pedestrians. After exploring the pond, we headed back, but veered off the trail in downtown Winchester to explore some more, before calling it a day after 4.6 miles. We still have one more section to go in order to complete the trail.

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After three days off from adventures, we were back at it! This is the last section of this bike trail that we had left. We walked a 2.5 mile stretch (5 miles out and back) between Winchester High School and Leland Park in Woburn, where we left off in April. Once past the high school, the greenway is routed on side streets with sidewalks for about three quarters of a mile, until we reach an elementary school where the dedicated trail picks up again. This portion passes through a couple different small parks before reaching Washington Street, where the trail once again is routed "on road" with sidewalks for pedestrians. The trail follows Washington Street for a short distance before turning down "D Street" near the cemeteries, and heads into Woburn. This was the least interesting portion of the trail, but a necessary walk if we wanted to complete the whole thing.

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