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Summer doesn’t end the moment the calendar flips to September — not around here, anyway. Between the shaded trails of South San Jose, the farm stands of San Martin, and the festivals that take over Downtown Morgan Hill every fall, late summer might be the best-kept secret of the year in South County. Here’s how we’re spending these last golden weeks before the weather turns.
Trade the Heat for the Trails
If you haven’t explored Santa Teresa County Park yet, now’s the time. With over 17 miles of trails winding through the Santa Teresa Hills, you get sweeping views of the Almaden and Santa Clara valleys without the crowds you’ll find at the more popular Bay Area parks. Prefer something with a little history? Almaden Quicksilver County Park covers more than 4,000 acres of old mining trails, perfect for a morning hike or mountain bike ride before it gets warm.
For an easier outing, the Coyote Creek Trail, especially the stretch between Hellyer Park and Bernal Road, stays almost entirely shaded, which makes it one of the most comfortable walks or bike rides in South San Jose even on a hot afternoon. And if you’re craving something family-friendly, Coyote Valley Open Space Preserve‘s 3.9-mile Arrowhead Loop is manageable for kids and adults alike.
Pack a picnic and head to Hellyer Park, where you’ll find disc golf, horseshoes, volleyball, and a playground that’ll keep the whole crew entertained.
Farm Stands and Farmers Markets
Late summer means peak harvest across San Martin and Gilroy’s farm country. Grab your reusable bags and stop by the Morgan Hill Certified Farmers’ Market, held every Saturday from 9am to 1pm at the Caltrain Station on Butterfield Blvd, or the weekly market on Depot Street downtown. You’ll find heirloom produce, local honey, and the kind of tomatoes that make you remember why we live here.
Sip Your Way Down the Wine Trail
South County’s wine country is hitting its stride right about now. The Santa Clara Valley Wine Trail loops through Gilroy, Morgan Hill, and San Martin, connecting dozens of family-run wineries — many of which host live music, sip-and-shop nights, and harvest celebrations as the grapes come in. If you’ve never used the local Trail Pass for discounts at participating wineries, late summer is the perfect excuse to start.
Mark Your Calendar: End-of-Summer Festivals
Two of South County’s best community events land right at the close of the season:
Taste of Morgan Hill takes over Downtown Morgan Hill on September 26–27, 2026. This free, family-friendly festival is one of the best ways to sample local restaurants, breweries, and wineries all in one place.
The same weekend, Gilroy’s Annual Tamale Festival & Car Show rolls into town on Saturday, September 26, 2026, combining classic cars with some of the best homemade tamales in the region.
Why We Love This Time of Year
There’s something about late summer in South San Jose and Morgan Hill — the trails are quieter, the produce is at its best, and the whole community comes together for one last round of festivals before fall settles in. It’s also a great time to fall in love with a neighborhood you haven’t spent much time in yet, whether that’s a quiet cul-de-sac near Santa Teresa or a vineyard-view lot in San Martin.
If any of these spots have you dreaming about what it would be like to actually live nearby, I’d love to help you explore what’s available. Send me a message or give me a call — let’s find your next home before summer’s officially over.
Bonnie Michalek
(408) 981-9201
bonnie.michalek@cbrealty.com
Serving San Jose, Morgan Hill, San Martin & Gilroy
