West of Trail

Delivering neighborhood connections to your mailbox every month.

Man holding baby to meet another baby in stroller.

Welcome! Let’s get to know our neighbors.

We know genuine connections with neighbors next door and business owners down the street make for a more meaningful experience. And we believe getting to know people in our community should be simple. That’s why Stroll meets you where you’re at – your mailbox.

We are grateful to serve this amazing community.

Every month, we share stories from and about different residents within our neighborhood.

See below for a few of our recent favorites.

Florence, Italy
An Attitude of Gratitude:

The Happy Ordonez Family

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Rides to Remember: The SRQ Trolley of Sarasota
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Chairs Ethan & Molly Biter, Sepi & Ryan Ackerman
Cooking for the Arts - A Sold-Out Success for Southside Elementary

Bringing the Community Together to Support the Next Generation of Artists

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Maggie being presented by her father John May
Grace, Leadership & Community

Recognizing Our 2025 Neighborhood Debutantes

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Ricotta Gelato
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Eric Fenton, Developer (with BelpointeREIT) of Aster and Links & his mom and raffle prize winner, Linda Fenton
Love, Laughter, and Community

Valentine’s Neighbors’ Night Out

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Winner Winner…Fish Dinner!

The Rockstar Offshore Tournament

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Ellen & Sheldon Rich with Bandi
Meet Ellen Rich

Lifelong Dog Lover and Award-Winning Barbet Exhibitor

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April Community Happenings

Your guide to local gatherings, social events, and neighborhood fun!

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Growing Gardens

A Century in the Making: Southside’s Garden of Legacy

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Advertising Partners

Stroll is made possible by the great local businesses who support this magazine. If you’re ever in need, please keep them in mind!

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Meet Your Publisher

Sarah Massey

Sarah Massey

Sarah Massey, Stroll West of Trail publisher, created the publication in 2013. Sarah grew up in the neighborhood, so for her, this is the perfect way to show her gratitude to this wonderful community. Sarah currently lives in the area with her husband and two children. They enjoy going to the beach, swimming, playing sports, and relaxing with friends and family.

A connection to Neighborhoods: Avondale, Bay Point Park, Cherokee Park, Harbor Acres, Hudson Bayou, McClellan Park, Shoreland Woods, and South Poinsettia Park, Oyster Bay, San Remo, Granada and Kentwood Estates. In each issue, you will discover a collection of fun and thought-provoking stories written by your neighbors on a variety of topics ranging from homes, families, pets, travel, recipes, and more! Whether you're a new or long-time resident, Stroll Southside Village is an excellent way to keep up with the community, meet new friends, and discover some of the finest local companies to do business with.

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