Introduction

As part of my “passionate pursuit”, I’ve decided to explore and share cycling routes around Olin College of Engineering. I’ve been cycling around Olin for a while now — anywhere from a 5-minute ride to Wellesley College to a 3-hour loop around towns like Dover, Sherborn, and Medfield. I’ve been using Strava to track my rides, and I’m going to use this post as a way to share some of my favorite routes. By doing so, I’m hoping to inspire others to explore the area and enjoy the beautiful scenery that surrounds Olin, as well as make cycling more accessible to the community.

Context

I’m a 23-year-old male with a diverse set of fitness background (running, climbing, weightlifting, swimming, calisthenics, hiking, etc.) so please keep that in mind when you’re reading through this post. I’ve been cycling (very) casually for about 16 years now, mostly as a mode of transportation, but I’ve been doing it more seriously since the past summer for longer rides. I’ve done metric centuries, but by no means am I a great/experienced cyclist.

As a student without a car, I’ve cycled to get groceries, get to events, commute to work, as well as for fun. I’m going to mainly share routes that are longer than 40 miles since those are the most intimidating if you aren’t sure what the road will actually look like beyond Google Maps (or other route planners). I’ll also share some tips on how to make your ride more enjoyable, and some things to keep in mind when you’re out on the road.

Routes

(Credit goes to Cassandre Roos ‘25 for the taking me on all these routes!)

The first route is a nice loop that has a mix of flats and hills. Although there are some portions where traffic can be a bit heavy, the majority of the route is on quiet roads with beautiful scenery.

The second route is goes through Mass Central Rail Trail, which is a really nice paved path, but the route also has segments on the road with quite a bit of cars. Avoid apple picking season since it goes through popular orchards and the traffic can be quite heavy even in weekend mornings.

The third route is a slightly longer route that goes up north to Concord. It’s a nice route with pretty views and a lot of empty country roads.

Bonus route

For a bonus route, I’d like to share my route that I take to commute to work. It’s a decently short route that will take you to Cambridge from Olin. If you cut it short, you can also get to Boston. I really enjoyed commuting on my bike because it got me to work faster than any other mode of transportation, and it was a great way to get some exercise in during the week. The only downside is that you have to start early enough to beat the heavy traffic in the rush hour. I generally left around 6 AM from Olin and left around 1 PM from work to avoid the worst of the traffic. When I first started commuting, it took me about an hour, but I got it down to 45 minutes once I got used to the terrain and turns.

Tips

• Stay visible: Wear bright colors, use lights, and make sure you’re visible to drivers.

I’m a big fan of black in clothing, but this can be quite dangerous when you’re cycling in the dark or low contrast environments. Plus, if it’s summer, you’ll be sweating a lot more in black. Also, use lights when it’s dark or when visibility is low.

This may be a controversial take, but I sometimes intentially cycle in the middle of the road when the shoulder is narrow and there is no bike lane. This is to prevent cars from squeezing by me and potentially hitting me. If you’re in the middle, they can’t pass you unless they go into the other lane or you let them pass, which is a much safer option. Drivers might honk/flicker at you, but at least you’d be aware that they’re going to pass you. Most of the time, they’ll just wait until it’s safe to pass you. You should also try to let them pass by gesturing or moving to the side you as soon as it’s safe to do so.

• Stay vigilant: Cars and pedestrians can be unpredictable, so always be on the lookout and be ready to dodge.

It’s important to assume that cars and pedestrians could act unpredictably and unintuitively. For example, cars might not signal their turns, or pedestrians might suddenly cross the street without looking. Try to anticipate these actions and be ready to react quickly. Keeping a safe distance makes this easier.

• Stay predictable: Signal your turns, follow the rules of the road, and be reasonable.

Similar to how you should anticipate others’ actions, you should also make sure that others can anticipate your actions. Signal your turns, stop at stop signs, and follow the rules of the road. This makes it easier for others to predict what you’re going to do and reduces the chances of accidents. This is especially important when cycling on road shared with cars since they’ll often be very close to you and they’ll not be able to react to your sudden movements. It also makes you a more responsible cyclist, which is important for the reputation of cyclists as a whole.

• Stay prepared: Bring water, snacks, tools, wallet, and a phone.

You probably already know that you need water and snacks for longer rides, but it’s also important to bring tools, wallet, and a phone. Tools can help you fix minor issues on the road, wallet can help you buy things or get help, and a phone can help you navigate, or call for help. I recommend at least a multitool, a tire fixing kit, a pump, some cash, and a phone. Bonus points if you can bring your insurance card as well.