I had to look up the location of the Daly Rink, and it seems you were off the bikepath by a few blocks. DcSe
gave a nice description of the entire length of the Charles River Bike Path. I have not ridden myself from Watertown to Waltham, but I estimate the entire loop would be about 20 miles. A couple other suggestions are the Minuteman Bikepath from Arlington Center to Bedford, about 11 miles one-way. It’s entirely paved and mostly leafy green scenery and it passes close to historic Lexington Center with nice casual restaurants, and the historic Minuteman statue.
A more urban path is the Southwest Corridor Path beginning in the Back Bay by the Train Station and proceeding to Forest Hills, At Forest Hills you can enter the Arnold Arboretum for some gentle parkland riding. I would estimate that ride would be about 15 miles or so round-trip.
There are some interesting Columbus Weekend events in Boston, including the Tufts 10K Women's Road Race in downtown Boston, an Oktoberfest in Harvard Square in Cambridge, and a Street Performer's Festival at Quincy Market. As you realize, the farther out from downtown, the cheaper the hotels. You might consider some hotels on the Rte 128 Beltway in Waltham, because that would provide easy access (by car) onto Mass Pike and into downtown. A cousin of mine stayed at the Westin if I recall, with a reasonable rate one September.
BTW, Boston and has a bike sharing system called Hubway
, and you could rent a bicycle on an hourly to daily rate from many kiosks, or rent a bike from several bike shops (likely cheaper on a daily basis). I would like to offer to show you around, but I have a busy but unfixed schedule for this weekend which would include some pleasure walking in downtown Boston if interested. Feel free to send me a PM for any further information I could provide. I enjoy showing people around Boston, and was the point man here for this year’s Fifth Annual Fifty-Plus Forum Ride.
I'm sure readers of this Northeast Regional subforum would enjoy reading of your experience here.
PS: FYA, the Charles River Bike Path is known as the Dr. Paul Dudley White Bike Path, who was President Eisenhower’s cardiologist when he had a heart attack circa 1955. Dr. White I believe was an early advocate of exercise for the heart. The Southwest Corridor Bike Path is known as the Pierre Lallement Bike Path:
Originally Posted by Wikipedia
[Lallement] is considered by some to be a the inventor of the bicycle… He died in obscurity in 1891 in Boston at the age of 47.