In late 1990's, three communities collaborated to design a recreational path, now known as the Tri-Community Greenway and Bikeway, which runs between Stoneham and Woburn by way of Winchester. It took over 10 years to complete planning and had to overcome many challenges. Construction started in 2017, and it was opened in 2018. It cost over $6 million, supported by state and federal transportation funds. Per AllTrails it is an easy 12.7 miles round trip out and back.
This section of the trail is not the most scenic, passing through a few business areas. However, it is quiet and free of a lot of traffic. There may be some muggles coming and going, so use some stealth as needed. Tweezers may be helpful.
UPDATE: Congrats to Geo-Knot for FTF and many thanks to Geo-Knot and SuretteFam for some guidance!