Upcoming Events on the Trail

We can't wait to see you!

Harvest Wine Weekend on the Pleasant Valley Wine Trail

October 20-22, 2023

Join us as we celebrate Harvest 2023!

Our wineries are planning a weekend of dinners, live music, barrel tastings, wine specials and more! Check back often to be the first to learn of newly added events.


Winemaker's Dinner at Bon Niche Cellars

Saturday, October 21, 2023


Join us on the patio for a sunset and catered dinner by Chef Mike and Chef Dawn of Knife+Fork - a five-course paired meal with Melani’s fall releases. Menu coming soon.

Limited seats available – this event will sell out! 


Paella Party at Four Sisters Ranch

Sunday, October 22, 2023


Join us as we celebrate Harvest 2023 with Paella from Junction Tapas and LIVE MUSIC from The Breedloves (back by popular demand).

$25 per person, includes paella and glass of 2018 Tilden Tempranillo/Grenache blend

$15 per person, wine club

Advance reservations required - call 805-467-2046.

Shrimp Boil and Live Music at Tackitt Family Vineyards

Saturday, October 21, 2023


All you can eat shrimp boil with potatoes, corn, sausage, and fresh baked bread by Linda and Gary Bouchard!

LIVE MUSIC by Rolf Gehrung.

$80 per person, includes first glass of Tackitt Family Vineyards wine.

$65 per person, Wine Club, includes first glass of Tackitt Family Vineyards wine.


Live Music at Cinquain Cellars

Saturday, October 21


Enjoy the tunes from local guitarist Adam Levine.

October 21 & 22. 11am-4pm

Wine tasting all weekend - appointments NOT required for this festival weekend, but can be made on our website.


Live Music & Food Trucks at Locatelli Vineyards & Winery

Saturday, October 21 1-4pm

Music by Julie Beaver

Food by SLO Meltdown

Petite Sirah vertical tasting including 2022 vintage in barrel.

Sunday, October 22 1-4pm

Music by Canyon Rose

Food Truck TBD

Petite Sirah vertical tasting including 2022 vintage in barrel

Fall Release Party at Mystic Hills

Saturday, October 21 12-4pm

Music, food, and the release of our 2019's. Wine club and guests - all are welcome! Please let us know you are coming. Email us to r.s.v.p. or give us a call at 805-610-1099.


"Amazing World of Bees" at California Lavender Honey Farm

October 22, 2023 10am

To celebrate the fall honey harvest, visit California Lavender Honey Farm for the "Amazing World of Bees" tour.

Learn about the fascinating world of bees and beekeeping, tour the unique Bee Museum & taste some delicious freshly harvested honey! This is a small group tour so prior registration is required - email mycaliforniafarm@gmail.com

Price: $25 for adults, $10 kids ages 5-15, kids under 5 - free. 

Bonus #1: The farm stand will be open TO ALL from 8:30 to 10:30am for visitors to purchase delicious, freshly picked produce, including many varieties of heirloom tomatoes. 6380 Hawk Ridge Pl, San Miguel

Bonus #2: The farm will be beautifully decorated for fall so you will be able to take season photos with your friends and family - available for tour guests only.


Paint & Sip at Graveyard Vineyards

Saturday, October 14th 12-2pm

Enjoy some Halloween fun painting on barrel staves with Karyn of ArtSocial 805.

Tickets: $55pp - includes your first glass of wine and your very own piece of art to take home! All supplies are provided. No painting experience required.


Live Music Series at Villa San Juliette

October 1, 8, 15 ,22 1-4pm

Celebrate fall each Sunday in October wine and music - the perfect pairing!

Two We experiences to enjoy: Make a reservation for a full tasting flight and Chef’s lunch menu on the patio.– OR –Indulge in bottle service and relax on the lawn, no reservations needed.


Other Trail Events for 2023

Cans for Cabs Annual Food Drive - November 3-12

Help support families in need. Join the members of the Pleasant Valley Wine Trail this season of giving during our Annual Cans for Cabs food drive.
When you visit Pleasant Valley Wine Trail members November 3-12, bring packaged, non-perishable food items to donate and enjoy special discounts or perks as our thank you.

Holiday on the Trail Annual Toy Drive - December 1-5

You're invited to visit our tasting rooms, located in the beautiful rolling hills of San Miguel, the weekend of December 1-5, 11am-5pm, to drop off donations of new, unwrapped toys. Visitors with donations will enjoy “perks” like free tastings, special tastings, wine discounts, and more!