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Best events in
Middletown

Looking for events or things to do in Middletown, CA? The local scene moves at a comfortable pace, with a focus on community gatherings and arts. Entertainment often centers on live music and comedy at the Twin Pine Casino or creative workshops at the Middletown Art Center.

Explore downtown Middletown's historic main street for a quiet meal before heading to a local show or gathering.
Catch a comedy show or live music performance at the Twin Pine Casino & Hotel, a primary destination for evening entertainment.
Discover local creativity at the Middletown Art Center, which hosts events like the monthly Monthly Makers' Fair and various exhibitions.

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50th Anniversary Field Trip - North County - Legacy Lands

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DIY Holiday Garland

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Wine Tasting & Party for Single Professionals in the Sonoma Wine Country

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Bienvenue Vineyards Wine Lounge

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Taste Destination 128 Soup & Sweaters Holiday Soirée

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Merry Mahjong at Montage Healdsburg

Sun, Dec 13 • 2:30 PM

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Aeternum – Rejoice and Be Merry!

Sat, Dec 19 • 6:00 PM

Clos Pegase Winery

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Sip, Sort, Win - Speed Puzzle Competition primary image

Sip, Sort, Win - Speed Puzzle Competition

Fri, Nov 6 • 6:00 PM

Tasting Notes - Wine Lounge Collective

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Wine, History and Community in Sonoma 2026 primary image

Wine, History and Community in Sonoma 2026

Sat, Nov 7 • 11:00 AM

Paradise Ridge Winery

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50th Anniversary Field Trip - North County - Legacy Lands primary image

50th Anniversary Field Trip - North County - Legacy Lands

Sat, Nov 14 • 10:00 AM

SLT Office -- Trip to North County

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DIY Holiday Garland primary image

DIY Holiday Garland

Sun, Nov 15 • 1:00 PM

Tasting Notes - Wine Lounge Collective

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Wine Tasting & Party for Single Professionals in the Sonoma Wine Country primary image

Wine Tasting & Party for Single Professionals in the Sonoma Wine Country

Sun, Nov 22 • 3:00 PM

Bienvenue Vineyards Wine Lounge

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Taste Destination 128 Soup & Sweaters Holiday Soirée primary image

Taste Destination 128 Soup & Sweaters Holiday Soirée

Sat, Dec 5 • 11:00 AM

Alexander Valley

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Merry Mahjong at Montage Healdsburg primary image

Merry Mahjong at Montage Healdsburg

Sun, Dec 13 • 2:30 PM

Merry Mahjong at Montage Healdsburg

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Aeternum – Rejoice and Be Merry! primary image

Aeternum – Rejoice and Be Merry!

Sat, Dec 19 • 6:00 PM

Clos Pegase Winery

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Thu, Nov 12 • 7:00 PM EST

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Online Group Reading Nov 1 | Psychic Medium Michelle Russell

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No Title, No Permission, No Problem: Harnessing the Power of Influence

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Frequently asked questions about Middletown

Where can I find comedy shows in Middletown?

The Twin Pine Casino & Hotel regularly hosts comedy nights. This venue is a primary spot for evening entertainment, offering a lineup of stand-up performances and other live shows in its event spaces.

Are there free events in Middletown, CA?

The Middletown Library offers many free activities for the community. These often include craft events, a weekly chess club, and Nintendo Switch gaming sessions for various age groups.

What kind of art events happen in Middletown?

Middletown's art scene centers on the Middletown Art Center (MAC). The center hosts rotating exhibitions, workshops, and a monthly Monthly Makers' Fair featuring local artists and live music.

What is the nightlife like in Middletown?

Middletown's nightlife is relaxed, often involving a show or dancing. The Twin Pine Casino is the main hub for late-night entertainment, while Noble's Saloon offers a historic, traditional bar atmosphere downtown.

What are some family-friendly things to do in Middletown?

Middletown Central Park is a great spot for family-friendly activities. The park hosts the annual Middletown Days festival each June and provides open space for community gatherings and outdoor recreation.

Where are the best places to see live music events?

Live music events are frequently held at the Twin Pine Casino & Hotel. Additionally, the Middletown Art Center often features musical performances during its monthly Monthly Makers' Fair, showcasing local talent.

What kind of things are there to do in downtown Middletown?

Downtown Middletown offers a charming, historic main street for a stroll. Its quaint shops, local restaurants, and historic spots like Noble's Saloon provide a relaxing way to spend an afternoon or evening.

Does Middletown have any big annual events?

The largest annual event is Middletown Days, held each June. This multi-day festival at Middletown Central Park features a parade, rodeo, live music, and other community-focused activities.