Upcoming Events
From time to time, we host special small-group experiences. We hope you’ll join us at the next event!
April 2026
Adult Easter Egg Hunt
Why should kids get all the fun on Easter? Join us for a free adult Easter egg hunt at 1 PM on Sunday, 4/5, with candy and special prizes!
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Crown Club Saturday: Tulip Field Days Happy Hour
Join us on Saturday, April 11, for a unique happy hour experience among the blooming tulips at Chiles Peach Orchard!
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Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
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May 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Crown Club Saturday: Vineyard Walk
Club members are invited to an exclusive behind-the-scenes walk through the vineyard. RSVP in advance!
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Karaoke Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
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Chiswell Book Club May Meeting
Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
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Sippin’ Monday: Memorial Day
Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, May 25, 2026.
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June 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
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Crown Club Saturday: Summer Picnic
Members and their guests are invited to our annual summer picnic on 6/13, featuring Brownsville Market’s fried chicken! Sign up by June 8.
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Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
July 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Karaoke Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
Chiswell Book Club July Meeting
Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
More Details
August 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
September 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Sippin’ Monday: Labor Day
Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, September 7, 2026.
More Details
Karaoke Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
October 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
December 2026
Holiday Open House
Join us for live music, Christmas cookies, and traditional mulled wine at our holiday open house on Friday, December 18.
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Wedding Events
Beyond our seasonal calendar of unique winery events, Chiswell boasts a gorgeous outdoor space to host wedding ceremonies and celebrations. With stunning outdoor views and a selection of award-winning wine, we hope that the property will serve as a grounding place to begin this next chapter in your life.
