Wineries with Live Music in Monterey Wine Country

If you're mapping out a weekend in Monterey Wine Country, do yourself a favor and build it around the music. Up and down the coast, from Carmel Valley Village to River Road in the Santa Lucia Highlands to the streets of downtown Monterey, tasting rooms turn their patios into stages all summer long. Think local singer-songwriters, cover bands, and the occasional touring act, all performing with vineyard views and a glass of something cold. Whether you're driving in for the weekend or just looking for wineries with music close to home, here's your lineup.

And since most of these stops are an easy day trip from San Jose and the South Bay, we've got you covered for the drive down too.

First, a Pit Stop in Los Gatos or Gilroy

There's no better way to enjoy wine country in Los Gatos than with live music in the courtyard at Testarossa. Testarossa sources single-vineyard Chardonnay and Pinot Noir from some of the best vineyards in the Santa Lucia Highlands and shares its latest vintages and exclusive library wines at its wine bar every day. Thursday and Sunday afternoons, they feature live music in the courtyard.

Just down the road in Gilroy, Sarah's Vineyard is worth the detour too, with live music the second Thursday of each month and often on weekends as well.

Gather your friends, reserve your table, and make it a relaxing afternoon or evening of wine, food, and music at Testarossa, and a perfect halfway point on the drive down to Monterey to begin your music exploration.

A Whole Village of Wineries with Music

With an unusual number of wineries packed into a few walkable blocks, add live music with your wine tasting to the long list of things to do in Carmel Valley on a summer weekend.

Folktale Winery & Vineyards features casual trios and touring headliners all summer in their mid-valley winery. The Wine Garden Music Series is casual and complimentary. Local singer-songwriters play on a rotating basis while you settle into a tasting flight or a wood-fired flatbread on the patio. No ticket required, just show up.

Live in the Vines is the main event: a ticketed concert series co-presented with Carmel’s local KRML Radio with bands like Briscoe and The Deslondes, bringing touring musicians to the winery with table service included. Treat this one like a proper night out.

McIntyre Family Wines hosts its “Music on the Patio” series every Sunday from July through September. Order a wine flight and snacks, or share a bottle while local artists play in the sunshine. It's also dog- and family-friendly, indoors or out.

I Brand Winery rounds out the Village stop with live acoustic music on the second Friday of every month at their Carmel Valley Village tasting room. It's a relaxed pairing with wines from acclaimed winemaker Ian Brand — an easy add to the two stops above.

Santa Lucia Highlands & Downtown Monterey

Odonata Winery leans all the way into summer. They’re open with longer summer hours, the perfect way to wind down your week with food trucks rolling in on the 2nd and 4th Friday of each month. Check their website for more information.

Puma Road & Pessagno “Tastings & Tunes”

Puma Road and Pessagno Winery run parallel music series at two different locations — worth knowing the difference before you plan your route:

• Puma Road at Portola Plaza, on Alvarado Street in downtown Monterey: live sets Friday and Saturday evenings, with a rotating lineup of local artists all summer.
• Puma Road & Pessagno River Road tasting rooms: live music Saturday and Sunday afternoons, with pours alternating between Puma Road Winery and Pessagno Winery week to week.

Both make an easy add-on if you're already exploring River Road wine country or spending an evening downtown. No reservations required, just stop in and order your favorite wine.

Carmel-by-the-Sea

Every Saturday this summer, Taste Morgan turns up the volume — just a little. Enjoy live music on the patio while you sip cool-climate wines from one of California's most exciting appellations. Walk-ins are always welcome. Pair it with half-off summer tastings, waived with any $50 wine purchase. Saturdays May through July 2026.

De Tierra Vineyards hosts “Sunday Funday Live” every Sunday afternoon in the tasting room at Mission & 5th. A local musician plays acoustic sets while you work through a tasting flight of Central Coast wines.

Carmel Plaza's Summer Live Music Series is the free, family-friendly finale: live music in the open-air courtyard every Friday in July. Each week pairs a different local winery with a Plaza restaurant — this year's lineup features Scheid Family Wines and Blair Estate Wines.