Week 6 – Winchester Highlands

Last week runners were treated to cool temperatures, dry air, and an overcast sky. Most people would complain that their summer Sunday morning was like that, but not runners. The group embraced the opportunity for a run unencumbered by the heat of summer and ran strong with glowing smiles. The running we’ve done in the heat has shown to make us stronger, and it shows when the weather turns cool. This past week was a nice tease for what to expect in October half marathons and marathons… or even Iceland. This week won’t be as cool, but its August so…

Our route this week starts out heading to Winchester via Franklin Street. Take Main Street north (say hi to Clarence DeMar as you pass Ell Pond, our patron saint of running) to a left onto Franklin. Follow this through Franklin Square, up a big hill, past Stoneham High School to a set of lights at an intersection with Summer Street. Turn left there and wind your way over to Main Street in Stoneham. Cross Main over to Marble Street. Follow that as it crosses over I93 and becomes Forest Street in Winchester. Look for the water stop on your left on Eugene Street.

Going short? Turn around and come back over I93. Turn right at a set of lights onto ┬áPark Street. Follow Park until you get to Main Street where Friendly’s is. Turn right here and run the backside of Spot Pond following Main over I93, under I93, through a few hills to where you’ll turn left onto Elm Street, your first major street intersecting with Main Street. Follow Elm up to the rotary at Highland and Woodland Street. Hug the turn left at the hockey rink and run the front side of Spot Pond to Pond Street. Right on Pond, continuing onto West Wyoming at Grimsby’s and a left turn on Main Street will get you to the end of your 8.2 mile run.

Going long? From the water stop you’ll continue on Forest Street and turn left onto Highland Ave at the Winchester Hospital signs. Highland will bring you up to the hospital, turn left onto Reservoir Road and run along my favorite street of the SLR program. This road will loop along the fells and drop you back onto Highland where you turn left. Follow Highland all the way to its end. In there is a 5-way intersection that sometimes causes confusion, you want to go straight through. At the end of Highland will be a water stop. Enjoy.

After that water stop you want to turn right on Rte 38, Main Street in Winchester. This will take you to a small rotary, here you want to run around it counterclockwise, as if you’re driving it, skip the tiny first road and turn onto the next major road. There is a historic sign for Symmes something-or-other there to continue on Rte 38. You’ll bear right at a fork which will put you on Washington Street. At another 5-way intersection you’ll cross Mystic Valley Parkway and bear right onto Washington Street. If you find yourself running past Winchester High SChool you’re going the wrong way. Follow Washington Street to Forest Street, where Gingerbread Construction Company is. Turn right onto Forest, up some big hills back to the first water stop.

Now you’ll follow what the short route runners did. Follow Forest to Marble, turn right at Park, right at Main Street in Stoneham, left on Elm, left at the rotary by the hockey rink, right on Pond, left on Main and you’re done. (read the short route paragraph if you want more detail).

Water Stops. Two helpers besides myself would be useful. I know AJ was thinking of it. AJ? Anyone else?

ROLL CALL! Who’s in?

28 Responses to “Week 6 – Winchester Highlands”

  1. Regina Curran says:

    In for the short please Jim, thank you

  2. Denise Judware says:

    Ran 16 slow lonely miles today, running the Mary O’Donnell 5K tomorrow. So, see you all next weekend. Thanks.

  3. Matt Kerton says:

    In for the full.

  4. Gail Severt says:

    Jim, I can help with a water stop.

  5. Donna says:

    I am in for the short – Thank you!

  6. Tom Gorman says:

    In for the full

  7. Krissy says:

    In for the full. Thanks!

  8. Bill Riley says:

    In for the full

  9. Nedim says:

    IFTS. Thanks!

  10. Jessi says:

    I’ll be doing 6 before we meet and 12 with the club. See everyone tomorrow!!

  11. Paul Locke says:

    Lynda and I are in for the short…

    Can you check the map vs instructions for the 8.2? The map has us on the back side of the pond, going down Pond St to Grimnsby’s then back up to Melrose High School on Lynn Fells before returning to Brueggers. I think the way you described will end up with more than 8 miles (10.5?).

  12. Lois says:

    I’ll be your Eugene St. waterstop as I just want to do the middle 6 or so.

  13. Tanya OHara says:

    I’m in for the short. Ken is in for the full.

  14. Lauren Cossette says:

    In for the full.

  15. Jim Carson says:

    Right again Paul Locke… one more time and you get to run the show! Short route goes the front of Spot Pond past the zoo and along the LynnFells Parkway, long route goes goes around as described.

    I need to stop posting before I have my morning coffee.

  16. Ashley DeAcetis says:

    IFTF thanks Jim!

  17. Katie Sinnott says:

    I be there for the short…as described by Paul. Thanks Jim!

  18. Julie Galvin says:

    In for the short! J

  19. Don Keren says:

    In for the full

  20. Jessica Crispin says:

    In for the short. Thanks

  21. Jason Doucette says:


  22. Jen d says:

    I’m in for the full. Thank you!

  23. Joanne Piper says:

    Pretty sure im in for the half.

  24. Michelle Beaulieu says:

    Recently joined the Mystic Running crew and I am looking for people to do long runs with. Someone recommended checking out your Sunday runs. Would love to join in tomorrow for the full…just wondering on time!


  25. Jim Carson says:

    8AM, Brueggers.

  26. Glen Josephson says:

    In for the full.

  27. Tanya OHara says:

    Sorry guys, we can’t make it after all. Have fun!

  28. Joe Winslow says:


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