It seems the more things change the more they stay the same; to wit, Sarasota’s enduring love of living in neighborhoods west of the Trail. (West of Route 41—Tamiami Trail—that is, for those just becoming familiar with the city’s grid)
Neighborhoods including Oyster Bay, Cherokee Park, McClellan Park and Harbor Acres—in roughly the area west of Route 41, between Mound Street (to the north) and Field Road (to the south)—are considered by many to be mainland Sarasota’s gold standard, residentially speaking. Walk-able, bike-able—and for many yacht-able and kayak-able—these long-established canal and waterfront neighborhoods are prized not just for their mature natural beauty but also for being in the middle of everything that makes the city tick—its best stores and boutiques, bars and nightclubs, restaurants and gourmet food markets; to say nothing of its top-rated schools and hospital (and surrounding doctors’ offices) and, of course its supremely gorgeous bay front. Once considered remote from downtown Sarasota (these neighborhoods were, after all, its earliest suburbs) they found themselves in the thick of things once the city began to spread out.
Living West-of-Trail hasn’t always been the ideal it is today. As automobiles became more available and easier to afford; and gas was cheap and plentiful, migrating to newer, more distant suburbs became the new normal. Suddenly it was a sign of upward mobility to live further away from town. Just as suddenly, areas west of Tamiami Trail were considered passé. Families, newly empowered to motor off in search of greener pastures, were demanding new homes on more spacious lots with plenty of room to grow and spread out—not to mention an attached garage (or two) to house their newest lifestyle accessory.
