Hi there, fellow Boston area cyclist here.

The best (and unforgettable) truly long ride is an all day affair, bike to Provincetown (tip of Cape Cod) from Boston (or somewhere outside of Boston) and take the ferry back that evening.

More reasonable long routes include going up and around Cape Ann (Gloucester, Rockport), out west to Wachusett mountain, or any of the local club weekend rides (Charles River wheelers has plenty of routes)

You can easily rack up 50+ miles just going up and around the near suburbs of Boston, such as Concord, Bedford, and Sudbury/Lincoln. These are all heavily biked towns with lots of wooded roads, strava segments, and flybys from all sorts of rippers to keep you motivated. There's almost always places to restock on water/food in the center of any given town.

I'll post some of my strava routes down below from past rides, although I'm curious to grab whatever others post as well as I've been looking for some new routes for myself lately. Most of my rides start from Somerville so honestly in West Newton you're already 10 miles closer to the "good stuff" in a lot of respects. Happy riding!

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Clubs/Affiliations: The Rippers / Charles River Wheelers / Cambridge Sports Union

Charles River Wheelers (http://www.crw.org) has a bunch of good routes in their library (including a Boston to PTown one); my favorite of theirs is the Apple Pi. 55-mile loop that starts/finishes in Bedford and goes through the apple farms in the Nashoba Valley area. Plenty of good quiet farm roads and some good hills to boot. Only downside is very few options on the route to get water etc if it is a hot day, but still a great ride nonetheless. Route is easy to follow with the pi symbol marked along the road.

Another good resource is the North Shore Cyclists route library (http://www.nscyc.org); I’ve ridden quite a few of these and they are great. Hope this helps, good luck!

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"You can never win or lose if you don't run the race." - Richard Butler

I echo both of the other replies. I moved to Newtonville in March (hey neighbor!) and have been thoroughly enjoying riding up through Weston before heading out to some of the other suburbs. I've had pretty good luck simply building routes on Strava's route builder. I have found that I much prefer heading out Commonwealth Avenue and then heading up through Meadowbrook to get into Weston and on to better roads. There are some speed humps but they aren't too annoying. That's the most efficient way I've found to get out of town, as I agree the roads in West Newton/Watertown leave a little to be desired.

Here's one I did a month or so ago, 65 miles, to give you a sense of the area I'm talking about. Note this was before I learned how to go up Meadowbrook and the first few miles weren't ideal, but once you get across 93 it's pretty smooth sailing. Happy to answer any questions if you have them!

https://www.strava.com/activities/3669825699

If you guys are ever up further north I live in Hampstead NH, exit 3 off 93N, and there are lots of good routes with minimal stopping (lights and such). I have some decent 50 to 60 mile routes with 2500' of elevation and you only stop once or twice if you don't make the light.

This is a bit of a drive but totally worth it: I recommend looking up flattest century in the east, it starts at UMass Dartmouth, which about an hour south (I grew up the next town over and live just north of Boston now). Takes me about 5:15-5:30 at around 200w NP and my totally unaero Allez. It’s a fun ride and you get some awesome coastal riding. Welcome to the area!

I live in Waltham so not far from you. Some of my routes:

Harvard via Oak Hill and Bare Hill. Also passes Harvard General Store twice: https://ridewithgps.com/routes/23906597
Thirtyish loop through Western Suburbs: https://ridewithgps.com/routes/33261385
The Apple Pi Ride described above: https://ridewithgps.com/routes/28113137
Wachusett from Waltham (haven't ridden this yet): https://ridewithgps.com/routes/28175422

I work at a College right on the Needham/Wellesley line, so often do intervals before work down in Dover (when actually on campus!), lots of nice roads down in that area as well.

I’m in Swellesley. I hate to be a Debbie Downer, but the riding here is bad to quite bad. If I’m Ironman training then I’m doing various random loops around Dover. You can get some ok riding going to Concord and beyond as well, but the roads are worse that general direction. I second the reco to look at Charles River Wheelman page. You will see their markings all over the road, so if you know where to start and what to look for on the road then that can help (though I guess a little outdated with today’s GPS map functions).

My suggestion for your long ride is to drive to the white mountains in NH and do some ride that involves the Kancamagus Hwy.

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Dimond Bikes Superfan

Honestly the Kanc was the most disappointing ride I've done. Terrain was cool, but I spent the while time getting buzzed by Harley's and clapped out econoboxes. The roads aren't buttery smooth but for longer rides I always head up towards Groton/ Townsend and quite like it.

Not to mention the Kanc is a 2+hour drive from Newton. There's tons of great riding west of 495 and empty roads west of Worcester.

CRW spent a lot of time building nice bike routes that don't use busy roads. However http://crw.org is a bit weird, it's not easy to use it as a repository of the routes. I remember about 5 years ago I was able to get dozens, now I cannot find them.

In any case, I've tried a lot. My favorite is https://www.crw.org/...east-european-ride-2 . A lot of medium-size hills, very few traffic lights and busy autoroad stretches.

If you're willing to drive southeast instead of north or west, here is my recommendation. Park at the visitor center in Wompatuck State Park and you can do a 75 mile loop that hits most of the south shore coastline:

https://www.strava.com/.../2723626965660996170

i've lived in most of the places mentioned: south shore, somerville, worcester (not western mass), pittsfield (definitely western mass) VT and now NH. if you like climbing like all good SF'ers do, head north to VT gaps or Kanc area . western ma like greylock is also pretty good. dont waste your free day near boston

Some good suggestions here. I great up in Newton, and when I first started riding in college, the roads out through Wellesley, Dover, Concord, Weston etc. were my escape route from the more crowded streets there. However, that was pre-smartphone, and every time I go back now, the Boston area traffic is worse and worse and I would imagine the road biking is also less safe. Some of those state highways are still so narrow, and everyone has too much horsepower in their cars and not enough focus on the road.

In addition to the recs above, I also recommend checking out northeastern Connecticut and the surrounding area of Mass and RI. There is great riding out here, lots of active cycling clubs, and much less traffic. It's also less than an hour from Newton (MA Pike then 395 south). You can even head in this direction from Newton or by driving outside of 495. Rev 3 was planning to introduce a 70.3 event in this area this year (postponed of course) from Webster MA, with lots of the bike portion covering great roads down into CT.

The best Boston area ride is the one that gets you the furthest away from Boston and keeps you there


#dontlookback

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"What's your claim?" - Ben Gravy
"Your best work is the work you're excited about" - Rick Rubin

Thanks everyone. These are great. And the CRW ride library is awesome. I definitely want to try the South Shore and Pi rides.

Here is what I’m leaning to for the Birthday ride.

https://www.crw.org/...nt/climb-clouds-2020

I’m thinking of going with the full century or the 80 mile option if weather forecast is super hot (so I get the main 2K climb up Mt Wachusett). Anyone familiar with that one?

So far the 2.5-3 hour rides I’ve done out west (Sudbury, Weston, Wayland) have been pretty good as far as road quality and traffic goes (though some of this could be empty roads due to COVID). Everyone told me the ride was so much worse than Bay Area and honestly it’s kind of exceeded expectations. The main thing I miss the most is the mountains (Mt Hamilton, Mt Diablo, Mt Tam, Kings, etc). Generally I used to rack up about 1K of climbing per 10 miles of riding. Out here it’s less than half that. And so far at least, I haven’t done any routes where to get that sense of complete remoteness you get like dropping drown the back side of Mt Hamilton or Morgan Territory. I’d really like to try to find a little of both of those things (mountains and remoteness) for the birthday ride.

I haven’t ridden this exact route but I have done Wachusett. I did it two years ago as part of a century when I was prepping for B2VT, starting in Bedford and following 62 to 70 to 140 and then coming up Mountain Rd and turning into the ski area before doing the summit road. That first mile or so up to the ski area entrance was pretty tough, but the road up to the summit actually had a few small dips and level areas that allowed for a quick brief respite before hitting the steep sections again. The descent coming down the other side of Mountain Rd and into Sterling on 62 was fun.

Wachusett Brewing Co. isn’t far from the mountain on 140, you should pick up some of their Green Monster IPA to celebrate your birthday ride. Good luck!

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"You can never win or lose if you don't run the race." - Richard Butler

I’d love to do the VT gaps. But unfortunately my wife is giving me a day not a weekend and I’ll be riding/driving alone. The gaps are a solid 3+ hour drive, so probably not logistically possible without an overnight on one end or a friend to split the driving. I find after these long rides I can really only handle 60-90 min each way.

I am not a resident, but here’s a few rides I’ve done on rented bikes when I was in the area:

https://strava.app.link/64z4PW7hx8
https://strava.app.link/VfzEuWaix8
https://strava.app.link/RNLsQbvix8

How is traffic on this route — the so called Notches around the Kanc Highway area in White Mountains NH? This looks like a solid 85 mile option with a splendid 6.5K of climbing, but it looks like it’s along some high speed stretches of road.

https://www.mapmyride.com/routes/view/20056056

The starting point in Lincoln is a 2 hour drive from my home (not ideal but do-able), but looks to be more remote than the Climb the Clouds route.

Thats a pretty classic ride, the traffic is never really "that" busy up there. Pretty much anywhere around the white mountains will be good.

-127 up and around Rockport is nice
-Head west from you out to Wachusett and back. There is a ton of riding and good roads from Concord west.
-Ride up to Portsmouth NH, along 1A

50/100 miles of "nice" riding is pretty easy to rack up cruising around just outside the city.

Oh c'mon! Nothing? Really?



You folks are WAAAAAAYYYYYY too serious - or maybe I'm too old?

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"What's your claim?" - Ben Gravy
"Your best work is the work you're excited about" - Rick Rubin

I didn’t notice the hashtag the first time. Nicely done.

Besides, the first album is much better.

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"You can never win or lose if you don't run the race." - Richard Butler

I agree

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"What's your claim?" - Ben Gravy
"Your best work is the work you're excited about" - Rick Rubin

that's the classic Kanc loop. traffic usually isn't bad, but these days with the Mass influx weekends are busier than usual, especially around the WMNF parking sites. week days are still pretty mellow, hopefully your birthday is a weekday. this is probably your best best for proximity , good roads, climbing etc