I can't think of anything worth doing in Brewster itself, except the Red Rooster on Rt 22, although I never venture off Rt 22 when I'm in the car, and only know the way to the trailhead from there.

But there is only one small climb right at the start of the trail, and then it is slightly uphill for about 3-4 miles, just enough to make you feel like you're having a bad cycling day, and then it levels off to Briarcliff Manor and then is downhill all the rest of the way. Or at least that hit feels when I've done it. And I've only done it one way, north to south. There's a park in Briarcliff with a swimming pool and a snack bar where I stop right off the trail, and that's when I'm usually thinking that I'll never make it, but then I fly. I must have done it as a round trip to there one time because I recall being there mid-day and the pool was open. Usually I do this ride when I'm coming back from the Berkshires and my wife drops me in Brewster at the trail, after a late lunch at the Red Rooster.

It is a 75 mile trip from Brewster to home. I did the whole ride the first time, but ran out of daylight the second time and took the subway from the Bronx. But this being the NYC subway, there was a problem and my train wasn't going through to Brooklyn, so I had to ride the last few miles in the dark with no lights.