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.

DISCLAIMER: This publication is owned by The N2 Company, and is not affiliated with or sponsored by any club, developer, or homeowners association.

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

See below for a few of our recent favorites.

Culinary Scholars 2026
A Legacy Baked with Purpose

How a cherished family memory inspired culinary opportunities for Sarasota’s next generation

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From Friendship to Forever

After seven years of shared adventures, Daniela and Graham celebrate a love story built on trust, intention, and the joy of growing together.

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Julie & Charlie Sizemore, Gina & David Warren, Melissa & Andy Douberly, Jonathan Warren, Tamara Brindley, Lisa Jayne Warren-Wallace & Tyson Babb, Rita R
Cooking for the Arts
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Simply Jo’s

Where Style, Community, and Heart Come Together

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July 2014
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August 2015
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Florida Irrigation
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June 2013
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Graduation from Pitt Law School, 2026
January 2015
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July 2013
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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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About Stroll

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