A big barrier to starting to ride again was finding places to go, particularly when trying to contend with Boston traffic. To avoid the second problem a bunch of my early rides were outside the city. This ride starts in Gloucester, where there is plenty of parking in city lots, and travels counter-clockwise around Cape Ann. Given that you are along the coast for the whole ride, it’s pretty flat although with some rollers. Not much traffic either, although we were there in the fall after peak tourist season. My wife joined me for this ride and it was her third time on a road bike, so definitely doable for someone without much experience. While not terribly challenging, the views are fantastic and ending up back in Gloucester means there are great opportunities for a post-ride meal.