Strategist Robin Hoberman Shares Her Favorite Running Routes in Westchester

Apr 22, 2022

What’s better than getting to know your neighborhood — and your neighbors — one run at a time?

Living in NYC for many years, I loved running along the East River, Central Park, through the NYC streets, the options were endless. As an avid runner, I was worried we would not have the same outdoor options in the Westchester suburbs. I learned very quickly how wrong I was. The suburbs are not only filled with wide sidewalks allowing for easy running, there are tons of running trails, the Hudson River, the Long Island Sound, plus so many amazing local run clubs. My suggestion for fellow runners is to throw your running shoes in the car and explore these towns on foot.

Here is my round-up of some of my favorite running spots throughout Westchester and parts of Connecticut.

Rye Brook — My Hometown!

Living in a small town means I can easily get to Greenwich, Rye, Port Chester, and Armonk for runs. I really love running to Rye Beach, local Crawford Park, through Lyons Park in Port Chester, or just exploring different local streets.

This past summer I joined up with the Port Chester Run Co, a local group launched by two NYC transplants who now call Port Chester “home.” The group meets on weekends and it’s been an amazing way to meet some local peeps from the area. Samantha and Billy, who started the run club, also own an incredible local coffee company.


Being on the Connecticut border I often run throughout the Greenwich streets. If you move to town, check out Greenwich Road Runners Club for weekly run meet-ups and races.

Tod’s Point Beach is another one of my favorite Greenwich routes. I park in town and run through the streets and local parks to get to the beach. It’s such a rewarding run. But even just running through the residential streets of Greenwich and onto Greenwich Ave makes for a great path. If you take this route, I recommend popping into The Granola Bar or Starbucks for a post-run treat.


The routes in Rye and through Rye Beach are amazing – you get scenic views of the Long Island Sound and have access to the sand. In the off-season, we love to bring our dog to the beach and in the summer we try to fit in some yoga at the beach pavilion.

Rye and Rye Park both have some great residential neighborhoods running, too. I’ve even snowshoed here in the winter! For a post-run snack, I love to end at Le Pain Quotidien.


The Aqueduct Trail spans the course of the Rivertowns to Yonkers. Yes, it’s a bit hilly, but it’s an excellent way to explore the various towns on the Hudson River. It’s a 20-mile trail so you can really make your route as long or as short as you want.

Sometimes I ask a friend to run with me and we take a break to walk over to the river, grab breakfast and walk back. There are some great local coffee shops (Bakehouse is one of the best) and farmers’ markets with live music in these towns.

You can even join the local run club, Rivertown Runners. They meet on the weekends to “put the fun back in running.” This group trains together for tons of events like the annual Sleepy Hollow Half, which I have run in.

Hudson River to Rockland County

Run across the Mario Cuomo Bridge (it’s over 3 miles each way) and spend some time in the beautiful village of Nyack. You’ll get amazing waterfront views from the bridge plus there are some excellent food, coffee, and shopping options. During my last run, we hit up Strawberry Place for coffee and breakfast. You can also find an amazing running trail at Nyack Beach State Park. Its located along the Hudson river with great views, the path goes for 4.5 miles.

White Plains/Valhalla

When I want a challenge, I hop over to The Kensico Dam. It’s just over a mile of beautiful running but there are some steps and trails that push you.

From here you can also hop on the Bronx River Parkway Trail and take a scenic run down to Yonkers.

Yorktown Heights

Franklin Roosevelt State Park is such a beautiful place to run. I switch it up between the paved and unpaved roads. There are two loops here that offer some excellent variety.


Rockefeller State Park Preserve is another awesome place to run. There are miles of great trails here with incredible views. It’s also home to the Stone Barns Center, which is one of the most peaceful places to stop in and grab a coffee.

There’s such a strong running community in Westchester. I love hitting the trails and seeing friends out for a run, too — and I’d love to see you pounding the pavement soon!

If you’re thinking about Westchester, I’d love to chat! I can even help you map out a route for your next visit to these towns. Reach out today so we can connect.

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