Week 6 – Winchester Highlands

Last week Gail and Hank took you out to Breakheart where you found some fun but challenging hills. While it is unlikely you’ll find hills like that in a marathon, what that run trains you for is the mentality to push through the miles after your legs have been challenged… something you’ll likely need to do in a marathon. This week we’ll take you over to Winchester and run through the Highlands. This route is longer and harder compared to the prior routes, but it is also a very scenic route, so sit back and enjoy the ride.

One note before I get into the details of the run, I’ve updated the calendar to the right. I added another week, after week 8, to adjust for the unusually late running of the Baystate Marathon. I also have added suggested milage for those training for Chicago. The marathon distances will read Baystate/Chicago distances. Chicago runners won’t have a route map with additional miles, but I’ll try to give you suggestions to add the extra miles in each week. This week I suggest everyone training for a marathon do about 16 and diverge starting next week. Of course, if you already have a plan you want to follow, feel free to deviate as needed.

This week’s 16 mile route was my favorite run when I ran marathons. We’ll run up Main Street past Ell Pond and give a nod to Clarence DeMar as you pass the pond. Continue past Whole Foods up to Franklin Street, where you’ll turn left. Follow Franklin into Stoneham, past Stoneham High School, to a light at Summer Street, where you’ll turn left. Stay single file on the curve of Summer Street and continue across Main Street in Stoneham onto Marble Street. Marble Street will become Forest Street in Winchester as you cross I-93. On your left  you’ll find the first water stop at Eugene Drive.

If you’re running short, you’ll turn back along Forest to Marble and turn right at the first set of lights you hit, on to Park Street. Park will take you over past Friendly’s, straight past the Stone Zoo, and along the front side of Spot Pond. Turn left onto Pond Street to head down to Grimsby’s, where you’ll turn left onto the  LynnFells Parkway. Take the parkway up past Melrose High School and turn right on Melrose Street to cut up to a right on Main Street, which will take you back to Brueggers.

If you’re running long, you’ll continue along Forest Street down to a left turn onto Highland Ave. There are blue hospital traffic signs to help point out where to turn. You’ll run up Highland Ave to the Winchester Hospital. Don’t go into the hospital, it’s not that hard of a run, instead turn left onto Reservoir Road. This is my favorite road to run on. You’ll come up to one of the Winchester Reservoirs in the Fells, running along with the Fells on your left and gaslight lamps and stately homes on your right (and a big hill in front of you). Enjoy the view as the road loops you back down to Highland Ave where you’ll turn left. Continue along Highland, even when you come to a 5 way intersection just go straight across to stay on Highland, until you get to the end where you’ll find water stop 2.

After water stop 2 take a right onto Rte 38, Main Street in Winchester. You’ll come to a rotary, pay attention here and follow these instructions as if you’re a car. Run counterclockwise into the rotary, passing a tiny street and taking the next exit out of the rotary staying on Main Street. There is a historical marker for Symmes Farm there. Stay on the right side of the road, as you’ll bear right onto Washington Street. Washington will bring you to another 5 way intersection where you’ll cross Mystic Valley Parkway and bear right to stay on Washington Street. If you run past a church you’re good, if you run past Winchester High School please turn around and try again. Washington will be a long flat run to the Gingerbread Construction Company where you’ll turn right onto Forest and run up a big series of hills to get back to the water stop on Eugene Drive.

After water stop 3 you’ll head back over I-93 and turn right at the lights onto Park Street. Run up to Main Street where Friendly’s is and turn right onto Rte 28 to run along the backside of Spot Pond. Turn left when you get to Elm Street, up to the rotary at Highland Ave, and go left there onto Woodland to find another water stop at the Flynn Hockey Rink in Medford (if I’m fast enough to get there in time for you). After the Flynn Rink follow the front side of Spot Pond to Pond Street, turning right down to Grimsby’s and straight on to West Wyoming. Turn left at the lights at Main Street and get yourself back to Brueggers.

Anyone looking for a mile more, turn left at Grimsby’s and take the LynnFells Parkway to Main Street, turning right to get back to Brueggers.

Water Stops. Hank and I will get Eugene Drive and Highland Ave. I’ll get over to the hockey rink to cover that stop.

If you need extra miles and can’t figure out how to add them on, let me know here and I’ll suggest some alterations.

Ok, who’s in? Roll Call!

32 Responses to “Week 6 – Winchester Highlands”

  1. Matt Kerton says:

    In for the full. Thanks Jim!

  2. Regina Curran says:

    Hi Jim

    Julie and I are in for the full, yikes!!!

    Thank you!

  3. Christina DiCalogero says:

    Jess and I are in for the short. Thank you.

  4. Nicole says:

    Iftf– thank u

  5. Judi Chiavetta says:

    Full, thanks!!

  6. Haecha Donnelly says:

    I’m in for at least half! Thanks!

  7. Stanley LeFave says:

    Myself and Raymond in for the full thanks to all

  8. Amy Giuliano says:

    IFTF. Thanks!

  9. Paul Locke says:

    In for the half

  10. Dan Slattery says:

    In for the full. 🙂
    I’m with you Jim, on favorite parts of certain routes: Horn Pond, Reservoir Rd., etc. for ex.

  11. Andrea Twomey says:

    I’m in for long

  12. Mike McLaughlin says:

    In for the full. Thanks

  13. Jessi says:

    Iftf!! Thanks so much!!

  14. Lee says:

    IFTF please. Thank you.

  15. Jen Bresnahan says:

    Me and Andy are in for the full. Thanks!!

  16. Lauren Cossette says:

    In for half + a couple extra.

  17. Brian Walfield says:

    Freddi’s in for about 10. I have no clue what I’m doing. Thanks Jim!!

  18. Pam says:

    IFTH, thanks.

  19. Lois says:

    IFTH, possibly beginning at Eugene.

  20. Lois says:

    i take that back about Eugene.

  21. Jackie Ecker says:

    In for the Half. Thanks!

  22. John E says:

    Doing the full! Thanks Jim.

  23. andy nagelin says:

    IFTH. Thanks Jim

    I have a watch power cord that I need to return to Kathi Rossi-Roh. Can I give the cord to someone to bring to the Tuesday night run?

    Thank you,


  24. Lynda Field says:

    In for some version of 8 miles will start at Main and Franklin when the middle group gets there (8:10ish?). Thanks Jim!!

  25. Liz hecht says:

    Jeanne and I are IFTH

  26. Oscar Dirks says:

    Oscar in for the full and Erin will do the half.

  27. Heather Lane says:

    Full please. Thank you.

  28. Jeff Rushton says:


  29. Alice says:

    I’m a maybe for the full. Thank you for all the options!!!!

  30. Kristen says:

    Ifth, thank you!

  31. Glen says:

    In for the full, Thanks!

Leave a Reply