The bulk of my vacation time the past few years, has been spent with me driving to a city with my bike and then biking around the city. Sometimes this has been to go on official bike rides with thousands of other people on closed streets and others it’s just me riding around town on bike paths or in the street. I absolutely love doing this. The big rides are fun because the towns usually route the ride through interesting neighborhoods and past important landmarks. And the individual rides are fun because it’s neat to learn your way around a new town. It’s also easy. I can put a destination in google maps and have it tell me directions best for biking.

As the weather gets chillier and I’m riding a little less (though not much as I want to ride through as much of winter as I can), I’m looking for other events or just fun places to ride. I’ll probably set up a regular webpage with information when I have more, but I just wanted to put down what I’ve found so far. One thing I’ve noticed when I searched for rides is that it’s a little difficult to determine if a ride is car-free or not. Since some people who I have biked with will only ride on closed-streets, it’s something I have to take into account.

Car-free Rides on the Road

  • Bike The Drive – Chicago
    My hometown ride that I’ve been doing for years. It’s always on the sunday before Memorial Day. Beautiful Lake Shore Drive is closed to traffic from around 6am to 9:30. It’s 30 miles of road that you can ride as many times as you want in the morning.
  • Five Boro Bike Tour – New York
    I’ve done this ride the last three years. It’s fun and you get to go to all five boroughs of New York. Two drawbacks for me. One is that the end of the ride is on Staten Island and you have to take a ferry back to Manhattan. There’s usually a pretty long wait for the ferry, though the free ride is pretty cool, since you can see the Statue of Liberty. The other is that there are a lot of people on this ride and it gets so congested in spots that you have to walk your bike. A third drawback for me personally is that it crosses a number of really high bridges and I’m slightly afraid of heights. Other people will probably not mind this at all. Total ride is around 40 miles, though you can take the Brooklyn Bridge back to make it shorter. This ride is the first weekend in June.
  • Tour de Troit – Detroit
    Just did this ride for the first time this year. Loved it. It’s around 28 miles all over Detroit. You get to see all sorts of different neighborhoods. It was a little crowded at the beginning, but then it turned into a lovely ride, even if it was lightly raining when we did it. I will definitely be going back next year. It’s in September.
  • Tour de Ille – Montreál
    I signed up for this ride this year, but couldn’t go. For me, this will be a little difficult to get to, but it looks to be an awesome ride. It’s 50km (31 miles) all over Montreál. It’s around the end of May/start of June. Definitely on my list.
  • Minneapolis Bike Tour – Minneapolis
    I just found out about this one and it looks like a good ride. Sadly, it also appears to be on the same day as the Tour de Troit. I will have to check the date for 2016 as I’d definitely like to do it. They have different lengths of 16, 25 and 32 mile routes. And I know Minneapolis is a very bike-friendly town, so I’d assume this would be a great ride.
  • Ride for the Arts – Milwaukee
    I’m not sure that this is 100% car-free as the map shows some roads as closed, but I can’t tell if they all are. This ride also has routes of various lengths. Drawback, for me, is that I think it’s the same day as Bike the Drive, but will have to double-check.
  • Pedal Pittsburgh – Pittsburgh
    This is another ride that I’m not certain is 100% car free. I have biked in Pittsburgh before (I love Pittsburgh) and one thing I should note is that it’s not flat. I rode up the steepest hill I’ve ever ridden here and while that was quite the challenge, I think the more terrifying part was the ride down. Note that I’m used to riding in the flat midwest, so hills are always a little crazy for me. Routes of various lengths and it’s usually at the end of August.
  • Tour de Nash – Nashville
    Again, not totally certain that the ride is 100% car free. The pictures on the website don’t show any cars, which makes me think it is, but I’m not sure. This ride is in May and they look to have three routes of different lengths.
  • Ride the Drive – Madison
    This is a closed road event, though it’s not just for bikes. The streets are closed from 8:30am to around 3pm for people to use the road for whatever they want. I can’t really tell how long the ride would be from end to end, but my guess is about 10 miles. For 2016, it’ll be on July 31st.
  • Hub on Wheels – Boston
    This ride is not completely car-free, though the 10 mile ride is. For the longer routes, you’ll share the road with cars. I have biked around Boston once and it was a lot of fun. I didn’t have any problems on the road, so I think this ride would be pretty good, even if you have to share the road with cars.
  • Acadia National Park Car-Free Mornings – Maine
    Two days in 2015, Acadia National Park closed the roads to cars. Don’t know if they’ll do it again in 2016, but that could be fun.
  • Ciclavia – Los Angeles
    Another place where they close the roads to allow people to do all sorts of things in the street. I haven’t gone to one of these, but they look like fun. One drawback that I’ve heard is that so many people come out, it can get very crowded in some places, which would make riding your bike difficult.

Other Places

  • Washington DC – I was in DC for the Cherry Blossom Festival last year and it was great fun riding my bike around town. There are lots of bike paths there and it’s easy to get around.
  • Philadelphia – I’ve heard that Philly is a nice place to bike because the roads are all pretty narrow so cars can’t travel that fast. They also just put in a new bike trail that I’ve heard is a really nice place to ride.
  • Maine Lighthouse Ride – Maine
    This is an organized ride where you share the road with cars. I’m looking into it because Maine is beautiful and I have a friend who lives in Canada not too far from there. So we could meet up to do the ride. It’s in September.
  • Tour de Lou – Louisville
    I signed up for this ride last year, but didn’t go because the weather looked really bad. It’s the start of Kentucky Derby Festival and looks to be an interesting ride. The road are not all closed, so that’s one drawback. It’s on May 1st, 2016.
  • Tour de Donut – Staunton, Illinois
    The only reason I’m including this is that it combines two of my favorite things in life, riding my bike and eating donuts. In general, I like riding in cities more, just because there’s more to look at. And this is partially a race and not just a leisurely ride, so it’s not high on my list of things to attend. But it has donuts…
  • Indianapolis – I’ve ridden the Cultural Trail and the Monon trail and they’re really nice. It was raining pretty hard when I rode them and I still had a great ride. There are plenty of places to stop and eat if you’d like. I’d definitely like to do this again.
  • Atlanta – Heard about a trail called the BeltLine. Could be nice
  • Portland – Everyone always says Portland, so I’ll have to get out there someday
  • Prince Edward Island – I’d think this would be really pretty.
  • Winnipeg – They have a pretty active biking community and a big bike week in June. They also have a ciclovia.

That’s all I have for now. I’ll try to make a more permanent page as I get more information.