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Cycling In Westchester County

Cycling in Westchester County -- Where Should I Start?
Coaches Corner — Coach Jon Reitzes

Cycling inWestchester County

Where should you start? It depends on where you are in your journey -- and that's a great place to begin.

One of the things I love most about coaching this team is that everyone comes in at a different place. Some of you have been riding for years. Some of you are just getting your bike out of the garage for the first time since last spring. And some of you are brand new to cycling altogether. All of that is completely fine -- that's exactly what this group is for.

Our group rides are designed to be fun, social, and progressive. We build mileage as the season goes on, we rotate locations to keep things fresh, and most importantly, we ride together. But here's the honest truth: if you have specific distance goals for the summer, our bi-weekly rides alone won't get you there. You'll need to be putting in miles on your own too.

Spin classes are fantastic -- I recommend them up to twice a week. They're great for your cardiovascular fitness, your leg strength, and your mental toughness. But after that, you really want to be on your own bike, moving through actual planet Earth. There's no substitute for it. You learn how to handle your bike, how to pace yourself, how to read terrain, and how to manage your energy over longer distances -- and none of that happens in a studio.

The goal is to build a handful of repeatable 15-20 mile routes near your house that you can knock out in about an hour. Doing the same routes consistently is actually a feature, not a bug -- it lets you track your progress week over week, watch your times improve, and feel the fitness building in real time. That's motivating in a way that varying routes constantly just isn't.

Not sure where to start near your neighborhood? Reach out and I'll help you map something. Seriously -- that's what I'm here for.

In the meantime, here are some great options right here in Westchester to get you started.

Route 01
North County Trailway
A beautifully paved former railway line running through the heart of Westchester -- this is one of the best dedicated cycling paths in the region. The rail trail surface is smooth, the grade is gentle (it was a train line, after all), and the scenery is gorgeous. It connects all the way up toward Mahopac as part of the Empire State Trail, so you can make it as long or as short as you like.
A word on rail trails: No cars is a gift -- but stay alert. Hikers, kids, dogs, and cyclists wearing headphones all share the path, and they don't always stay to the right. Ride with awareness, call out when passing, and keep your speed sensible around blind curves.
Route 02
South County Trailway
The South County Trailway is the southern counterpart to the North County, running from Yonkers up through the county on another paved rail trail. It's a great option for riders in the lower part of Westchester and connects with other trails to let you build longer rides. Same rules apply as the North County -- share the path and stay alert.
Route 03
Bronx River Parkway Cycling Sundays
This is a Westchester classic and genuinely one of the best things about living here. On designated Sunday mornings from May through October, a 13-mile stretch of the Bronx River Parkway is closed entirely to cars and opened up to cyclists, joggers, skaters, and walkers. It's a beautiful, car-free corridor through some of the prettiest parts of the county -- and a great way to get comfortable riding on a wider road surface without traffic. Perfect for newer riders building confidence.
Worth Joining
Westchester Cycling Club
If you want more miles, more company, and more structure, the Westchester Cycling Club is one of the best resources in the county. They run rides practically every day in the summer at varying difficulty levels, starting from different locations around Westchester. It's a welcoming community, and riding with more experienced cyclists is one of the fastest ways to improve. The price of entry is remarkably reasonable for what you get.
Membership: $40/year
Join the WCC →
Need a Route Near You?

Let's Map Your Home Base

Tell me your neighborhood and I'll help you build a repeatable 15-20 mile route you can ride all season. Watching your times drop on a familiar route is one of the best feelings in cycling.

See the Full Training Schedule →

Ride Schedule!

2026 Training Schedule -- Coach Jon
Breakthrough T1D — Westchester / NYC

2026 TrainingSchedule

Sign Up for Rides via signup genius →
Mar 14 2026
8:00 AM
Milton Point Provisions
5 Milton Point, Rye, NY 10580
Apr 11 2026
8:00 AM
Greenwich Municipal Parking Lot
Behind Saks Fifth Avenue, Greenwich, CT
Apr 25 2026
8:00 AM
Rye Neck High School
310 Hornridge Rd, Mamaroneck, NY 10543
May 9 2026
8:00 AM
Bedford Hills Train Station
60 S Bedford Rd, Bedford Hills, NY 10507
May 23 2026
8:00 AM
Chappaqua Train Station
1 Station Plaza, Chappaqua, NY 10514
Jun 6 2026
8:00 AM
SUNY Purchase
735 Anderson Hill Rd, Purchase, NY 10577
Jun 20 2026
8:00 AM
Greenwich Municipal Parking Lot
Behind Saks Fifth Avenue, Greenwich, CT
Jul 11 2026
8:00 AM
Milton Point Provisions
5 Milton Point, Rye, NY 10580
Jul 25 2026
8:00 AM
Bedford Hills Train Station
60 S Bedford Rd, Bedford Hills, NY 10507
Aug 8 2026
8:00 AM
SUNY Purchase
735 Anderson Hill Rd, Purchase, NY 10577
Sep 19 2026
8:00 AM
Seven Lakes Drive Parking Lot
Harriman State Park, NY
Oct 3 2026
8:00 AM
Location TBD
Check back for updates
TBD
Oct 17 2026
8:00 AM
Location TBD
Check back for updates
TBD
Oct 31 2026
8:00 AM
Location TBD
Check back for updates
TBD
Nov 14 2026
8:00 AM
Location TBD
Check back for updates
TBD

All rides depart at 8:00 AM sharp. Questions? Reach out to Coach Jon.

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Coach Jon Checking In -- Yes, Even in a Snowstorm

Doe, a deer!

Right now, we're in the middle of our second major snowfall of the season, and I know cycling may be the furthest thing from your mind. Fair enough. But here's the thing -- winter is actually one of the best times to lay a foundation for a strong ride. You don't need to be logging miles in a blizzard to make progress. A little intentional movement now, even indoors, can make a huge difference when the weather finally cooperates.

IS YOUR BIKE READY?

I know the feeling: "Where's my bike? I think it's in the garage... somewhere." March is the time to dig it out and bring it in to your local shop. Have the cables checked, the wheels trued, and the drivetrain cleaned of last year's gunk. I also like to start each spring with fresh handlebar tape -- it's a small thing, but it makes the bike feel new again.

While you're at it, there are a few basic maintenance skills every rider should have in their back pocket:

Lube your chain. Your chain and gears are metal on metal -- they need care. Pick up a bike-specific lubricant; I'm a fan of ceramic lube for the spring, which reduces friction, repels dirt, and lasts longer than standard wet or dry lubes. In the summer, I move to dry lube. To apply it, wipe your chain down with a clean rag first, then apply a single drop of lube to each link while slowly backpedaling. Let it sit for a few minutes, then wipe off the excess -- too much lube attracts grime. Over time, grit builds up, and you'll want to degrease the chain entirely before re-lubricating. A good rule of thumb: degrease every few months of regular riding, or whenever the chain starts looking gunky. This video is a great primer: https://www.youtube.com/watch?v=cqkitFhUq_4

Pump your tires before every ride. Yes, every single ride. Road bike tires run at high pressure -- typically 100 to 120 psi -- and they lose air even when sitting still. Make sure you have a quality floor pump with a gauge and know how to use it. This one step prevents a surprising number of problems out on the road.

Know how to change an inner tube. At some point, you will get a flat. It's not hard to fix, but it can be a pain if you're not prepared. Keep a spare tube, a set of tire levers, and either a small hand pump or a CO2 inflator in a saddle bag mounted under your seat. I also keep a multitool in there. Watch a YouTube video this winter and practice at home -- you'll be glad you did.

Know how to adjust your seat and handlebars. When bikes get transported, things get bumped out of position. And as your fitness and riding style evolve, you may want to make small adjustments. Understanding the basics here gives you flexibility and keeps you comfortable on long rides.

DO YOU NEED TO BUY A BIKE?

I'm jealous. New Bike Day is the best.

A few things to keep in mind: be honest with yourself about the type of rider you are right now, not the rider you hope to be someday. Don't buy a bike because you imagine yourself racing through Alpe d'Huez (and if that's actually your plan, again, I'm jealous). If your longest ride to date has been 10 miles and your goal is 50, get the bike that fits your current reality with that 50-mile goal in mind. If you're just getting started, the goal is to build a biking habit on a machine you genuinely love. That doesn't mean emptying your bank account. It means getting a bike that fits properly, is made of materials suited to your riding goals, and makes you feel good every time you swing a leg over it.

I love bike shops and believe strongly in having a relationship with your local one. That said, shops in our area vary widely in inventory and price point. Greenwich alone has three shops, each with a very different range. Some shops carry primarily high-end brands and simply don't have the floor space or inventory for moderately priced bikes. Know your budget going in, do a little research, and don't be afraid to visit a few shops before committing.

On that note -- fit matters more than price. A properly fitted $600 bike will be more enjoyable to ride than an improperly fitted $10,000 one. I guarantee it. Discomfort compounds over the miles, and a bike that doesn't fit will eventually make you not want to ride at all.

If you're buying new, go to a shop that will put you on a trainer, take your measurements, and order the right size and configuration for your body. If you're working with an existing bike or buying used, get a proper fitting done by a shop. They'll make sure your hips are square, your knees are aligned, your handlebars are set correctly, and your brakes and cables are in good shape. It's worth every penny.

A WORD ON SPIN CLASSES

Love them! Do them! But understand what they are -- and what they aren't.

Spin classes are typically under an hour, and the goal is to push you hard: max effort, strong heart and lungs, powerful legs. All of that is great training for any kind of riding. But a long outdoor ride is a different animal. Out on the road, we're playing the long game -- riding efficiently, using our gears to do the work, conserving energy, and yes, enjoying the moments when gravity does us a favor on a downhill.

If you're used to grinding it out in spin class and spending a lot of time out of the saddle, you may need to dial that back when you hit the road. To keep moving for five or six hours at a time, the goal is to go as far and as fast as possible while using the least amount of energy. It's a different mindset, and the sooner you start building it, the better.

SNACKS, SNACKS, SNACKS

Now is a great time to beta test your ride fuel.

One of the biggest differences between a 45-minute class and a full-day ride is that on the road, you need to refuel at least once an hour. I used to think of it in terms of carbs -- roughly 30 to 45 grams per hour -- but these days I find it easier to think in real food: a pack of M&Ms, half a sandwich, half a banana. You want something portable, easy to eat while moving, and most importantly, something you actually like.

Some of my go-to's: That's It bars, Made Good Granola Bites, and bananas. Start experimenting now so you know what works for your stomach before you're 30 miles in.

That's it for now! Let's hunker down in the storm -- maybe knock out a Peloton class or two -- and start getting excited for the road ahead. Check out my training schedule here and get signed up:

More soon. Stay warm and stay moving.

Ride on,

Coach Jon