Walk of the Town

Above: Meg Critchell and Heather Sargent have walked every single road in Greenwich.
Photograph by Venera Alexandrova

When Heather Sargent and Meg Critchell hiked through the Babcock Property on a July morning in 2015, they were amazed at how quickly the time passed, how many miles they covered and the beauty of their surroundings. The friends enjoyed the walk so much that Heather confessed she’d always wanted to “walk town.” Not stroll down the Avenue, but literally walk up and down every one of the 265 miles of paved roads in Greenwich’s sixty square miles. “Wouldn’t it be fun if we took a map and looked at all the streets?” Heather recalls saying to her friend. “I thought that Meg was going to be like, ‘You’re nuts,’ But she said, ‘Awesome!’” So Heather picked up the official map from Town Hall and began highlighting routes.

The two started with a four-mile walk on a 95-degree day down hilly John Street, across Porchuck and up to the Round Hill Store, passing a house with llamas and goats along the way. Soon, the moms were carving out early morning hours, and balancing their work schedules and kids’ activities to cover new territory, like the time they started from Meg’s house up Round Hill Road and headed south to Indian Harbor Yacht Club, walking up and down every dead-end street along the way—a twelve-mile trek.

Heather and Meg hit the halfway mark at the NYC Marathon

Though they would scope out some routes and use the MapMyWalk app to track their progress, they often set off without knowing exactly how far they’d be going. “There were a bunch of times when we’d walk too far, and we’d suddenly realize we’d walked twelve miles, we can’t turn around. We’d call a friend or one of our husbands and say, ‘Can you come get us?’” says Meg, who adds that they would text friends to ask them to leave water bottles in their mailboxes and occasionally wound up in Stamford or Armonk by accident.

On the streets they met all kinds of people who offered advice and encouragement, including a retired cop who urged them to wear reflective clothing, so they bought bright yellow jackets that they wore for the rest of their mission. They found themselves zigzagging the main arteries of town (Riversville, Lake, Round Hill, North Street and Stanwich), taking bathroom breaks at Nathaniel Witherell, discovering the Rosemary Hall Chapel up close, scoping out Halloween decorations in Glenville and Havemeyer and jumping the fence at Conyers Farm. “One of the things that kept us going is that this town is so big, so amazing and diverse, the neighborhoods,” says Meg. “It feels so small-town.”

Even a joint celebration for their back-to-back October birthdays wound up as a walking excursion. They invited friends to join them on a jaunt from backcountry into Bedford to the Mexican restaurant Truck, where they gathered for lunch and margaritas.

Heather and Meg head to a birthday celebration in Bedford with their Walkarita recruits.

Sideways rain did not deter these walking ladies, whose nickname became The Walkaritas. As they trekked farther and faster around Greenwich—an average pace of 13.6-minute miles—Heather and Meg completed their goal of walking the whole town and ultimately joined a team for the New York City Marathon (yes, it’s possible to power-walk the marathon). As Team Walkaritas, they raised more than $29,000 for the JDRF in honor of Heather’s daughter, Schuyler, who has type 1 diabetes. Heather recalls how a runner friend of hers envied the way that she and Meg would experience the marathon. “When you’re running, all you’re thinking about is how to get to the finish line. But when you’re walking, you’re taking it all in, seeing the communities,” she says. “That opened my eyes to soak it all in.”

NYC Marathon mission complete


Take a break from your normal walking loop and get out and explore town by trying one of these routes or mapping out your own.


PARK AT the Audubon. You can add on to this walk by hitting the trails at the Audubon.
TURN RIGHT onto John and then right on Bedford (one of Heather and Meg’s favorite houses is on the corner of Bedford and John).
TURN RIGHT onto Riversville and back to the Audubon. For a longer variation on the loop, walk up and back Sterling Road off of Riversville.



PARK AT Second Congregational Church. You’ll pass many historic houses and Greenwich Academy along this route.
TURN LEFT out of the lot onto Maple and continue to North Maple.
TURN RIGHT on Husted, right on Parsonage, right on Ridgeview Avenue and back to North Maple to return to the church.



PARK AT Cos Cob Park. Visit the park’s September 11 Memorial and enjoy the views of Long Island Sound before or after this walk to Milbrook and back.
TURN LEFT Leaving the park, head left onto Sound Shore Drive.
TURN RIGHT onto Sachem, and take a quick left onto Cross Lane.
TURN RIGHT onto Indian Field to intersection with the Post Road.
TURN LEFT onto Post Road and left down Woodside Drive.
TURN RIGHT onto West Brother Drive.
TURN LEFT onto Orchard and around the Wildwood loop and up Overlook back to the Post Road.
TURN RIGHT onto Strickland and follow that back to Cos Cob Park.



PARK AT Banksville Shopping Center. From the New York border to the beach, this strenuous course is followed by people training for the marathon.
TURN RIGHT onto North Street and head south.
TURN LEFT onto Dingletown.
CROSS OVER Stanwich onto Cat Rock Road and follow to Valley Road.
TURN LEFT onto Valley and right onto Palmer Hill, crossing over Mianus Pond on the stone bridge.
TURN RIGHT onto Sheephill.
TURN LEFT onto North Sound Beach Avenue and continue across the Post Road to Sound Beach Ave., which will take you through Old Greenwich.
FUEL UP at Upper Crust Bagel Shop or Alpen Pantry while you’re in town. Continue down Sound Beach to the intersection with Shore Road.
TURN RIGHT and continue to Tod’s Point. Uber back or call a friend for a ride.



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