I bike as a hobby and also serve as the faculty adviser for the Harvard University Cycling Association (HUCA). Here are some relevant resources, mostly routes that start out from Cambridge. They're in a format suitable for downloading and putting on a GPS headunit (e.g., a Garmin).
- H2H (shortest): this is the most direct ride from Harvard (University) to Harvard (Mass.), coming back through Concord. ~63 miles.
- H2H + Fruitlands: the longest version of H2H, adding in a loop past the Fruitlands Museum (with a view of Mt. Wachusett) and coming back the longer way.
- Harvard "Hammer Ride": the traditional Wednesday morning fast group ride with a bit of rolling hills but no climbs (~40 miles).
- Allis Loop: Another rolling loop through Sudbury and Weston, for some reason seems to be more popular as a winter training ride (~45 miles). Named in honor of John Allis, HUCA's longtime former coach.
- Mt. Wachusett, home via Harvard: A pretty long and challenging ride to Mt. Wachusett Ski Resort, up to the top, and then home via Harvard (~110 miles, ~7000ft of climbing). This route takes you home from Harvard via Concord, pretty directly.
- Silver Hill Loop: A short ride (~30 miles, very little climbing). Good for a quick spin, or if you're starting out and don't just want to spin up the Minute Man Bike Path.
- Dover via Wells Ave. This ride takes you south-west (rather than just west towards Concord and beyond). It's a fairly decent way out of town in that direction, and takes you right past the location of the Wells Ave. training crit. After that it heads out to Dover and does a couple of loops there.
- Lost Lake (Littleton to Bedford). This is an alternative to going up Oak Hill to Harvard and takes you through the Lost Lake area and further north than some of the other routes. This route ends in Bedford. To get to the start point, follow any of the "H2H" routes to Littleton.
- Quabbin Reservoir Century. A scenic century with a moderate amount of climbing. The start/end point is an elementary school parking lot in Rutland.
In addition, here are a couple of useful Strava segments.
- Park Ave., Arlington. Good for hill repeats
- Eastern Ave., Arlington. More hill repeats
- Mystic TT. Excellent for intervals and to practice pace-lining. People can do intervals at their own pace and just go up and down Mystic Parkway, so no one gets dropped.
- Charlie Baker Time Trial (aka: CBTT). A 9.5 mile loop with only right turns and minimal traffic interaction, almost completely flat. Useful for longer intervals than Mystic TT, etc.