West of Trail

Delivering neighborhood connections to your mailbox every month.

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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.

A Legacy of Generosity: Celebrating Sarasota’s Leading Women

Honoring women who lead with generosity, integrity and humility while inspiring across generations and transforming lives through giving.

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Resident Recipe
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The Lovely Leemings
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Comfortable Care Dental South Trail
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Sara Harris, Kate Buckley, Tori Harless, Kat Aoude
Ladies Breakfast at Raining Berries
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October Community Happenings
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1924 existing map
DÉJÀ VU
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Maddox Santiano starts kindergarten at Southside
Back to School 2025
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Free Book Fairs Bring the Joy of Reading to Sarasota’s Title 1 Schools
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The most creative day in Sarasota

PINC—an acronym representing People, Ideas, Nature, and Community

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Sarasota Electrical

Powering Sarasota with Expertise, Integrity, and Heart

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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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