I’ve done the Westwood–>MIT commute about a dozen times now. I won’t say how long it takes me–again, I’m just getting started and quite slow–but there are a few things I still haven’t figured out yet. If you have thoughts on the below, most appreciated!

1. The most direct path for me is up Washington Street in Dedham and over Bellevue Hill. I don’t love this route because 1) Washington St is a bit hair-raising (until the bike path) and Bellevue Hill isn’t fun either up or down (especially in the dark or rain).  I have taken an alternative path that avoids Bellevue Hill though it involves a busy segment of Centre St I don’t love. There’s also a bit of a hill on Centre St. I’d love to avoid if I could, though I think the only way to do that would be Baker St to Spring St (which is as bad as Centre St). So far, so good.
2. From there to downtown Boston is pretty straightforward if I go up the Southwest Corridor / Pierre Lallement Bike Path. But I hate what comes next. Getting off the path at Mass Ave has been a bit difficult. Going until the end of the path at Dartmouth St is equally difficult. The best thing I’ve found is to stay on the path (or on the Columbus St. bike lane until West Newton, and then snake through Back Bay to the Mass Ave bridge. Any improvements over what I’m doing? I’ve seen a possibility of jumping off of the path to take Hemenway – no bike path but it would save a mile or so.
3. But I don’t love the Southwest Corridor because you have to stop so often. I counted about more than a dozen intersections, more than half of which had stoplights. So I have instead tried going up the Jamaicaway path, which is great except for a couple of things. First is getting to the Jamaicaway path in the first place. If I take my usual route up Washington St to Forest Hills, the quickest way I’ve found is to ride on the sidewalk (or through the park) to the Arborway rotary and then up the sidewalk to the pond. Another possibility, which is a bit safer but takes longer is to go up the Pierre Lallement bike path a bit and then head west. Instead continuing on South St to Centre St would be a bit faster, but then again you’re on South St and Centre St.
4. Another possibility for getting to Jamaicaway would be heading west around the Arnold Arboretum — the southern end is way too steep for me to go straight through it, and then I still have the reverse-Arborway problem. One way is to take W Roxbury Pkwy up to Grove/Newton/Pond, though I’ve driven through and those seem like narrow roads with lots of traffic.  Another way I haven’t tried but am thinking about is W Roxbury Pkwy but then snaking through the hospital and some residential and just meeting up with Pond just before the pathway starts.
5. Jamaicaway is great b/c there are few stops. You can pretty much go straight from getting on the path to Route 9 (Perkins St. light is usually green). Of course getting across Route 9 is a bit hairy, as is heading up Brookline Ave to the connector St that gets back on the Riverway but I can’t imagine any alternative to that. Then next bit o’ fun is getting from the end of the Riverway trail to the Fenway trail – I just don’t see a pleasant way to do it though maybe I need to try a few different paths. Thankfully it’s not all that tricky to get from the end of the Fenway path to Boylston and then Mass Ave (it’s close enough to the bridge that I can hack it).

Thanks for any help!