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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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Events near Middletown

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Lagree for a cause, fundraiser for breast cancer research

Tomorrow • 12:00 PM

9046 Brooks Rd S

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Fall Succulent Pumpkin arrangements

Sunday • 2:00 PM

Trecini Wine Lounge

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50th Anniversary Field Trip - Sonoma Coast

Sat, Oct 17 • 10:00 AM

SLT Office -- Trip to Sonoma Coast

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In Good Company x MOTHER Wine Country Retreat 2026

Tue, Oct 20 • 10:30 AM

Flowers Vineyards & Winery

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The Rocky Horror Show- The Live Musical!

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The California Theatre of Santa Rosa

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Heritage Healdsburg: Past & Present

Thu, Nov 12 • 6:00 PM

Villa Chanticleer

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An Aeternum Christmas at Clos Pegase Caves

Sat, Dec 19 • 6:00 PM

Clos Pegase Winery

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Pigs & Pinot 2027 | Tickets primary image

Pigs & Pinot 2027 | Tickets

Appellation Healdsburg

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Lagree for a cause, fundraiser for breast cancer research primary image

Lagree for a cause, fundraiser for breast cancer research

Tomorrow • 12:00 PM

9046 Brooks Rd S

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Fall Succulent Pumpkin arrangements primary image

Fall Succulent Pumpkin arrangements

Sunday • 2:00 PM

Trecini Wine Lounge

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50th Anniversary Field Trip - Sonoma Coast primary image

50th Anniversary Field Trip - Sonoma Coast

Sat, Oct 17 • 10:00 AM

SLT Office -- Trip to Sonoma Coast

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In Good Company x MOTHER Wine Country Retreat 2026 primary image

In Good Company x MOTHER Wine Country Retreat 2026

Tue, Oct 20 • 10:30 AM

Flowers Vineyards & Winery

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The Rocky Horror Show- The Live Musical! primary image

The Rocky Horror Show- The Live Musical!

Fri, Oct 23 • 8:00 PM

The California Theatre of Santa Rosa

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Heritage Healdsburg: Past & Present primary image

Heritage Healdsburg: Past & Present

Thu, Nov 12 • 6:00 PM

Villa Chanticleer

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An Aeternum Christmas at Clos Pegase Caves primary image

An Aeternum Christmas at Clos Pegase Caves

Sat, Dec 19 • 6:00 PM

Clos Pegase Winery

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Pigs & Pinot 2027 | Tickets primary image

Pigs & Pinot 2027 | Tickets

Appellation Healdsburg

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Nearby cities

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22 miles away

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36 miles away

Petaluma

36 miles away

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46 miles away

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16 miles away

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29 miles away

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27 miles away

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44 miles away

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42 miles away

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32 miles away

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47 miles away

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19 miles away

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29 miles away

Lakeport

25 miles away

Kelseyville

19 miles away

Point Reyes Station

49 miles away

Dixon

47 miles away

Lower Lake

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Santa Rosa

22 miles away

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36 miles away

Petaluma

36 miles away

Fairfield

46 miles away

Sebastopol

27 miles away

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46 miles away

Vallejo

49 miles away

Vacaville

44 miles away

Woodland

46 miles away

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49 miles away

Sonoma

33 miles away

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18 miles away

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16 miles away

Rohnert Park

29 miles away

Guerneville

27 miles away

American Canyon

44 miles away

Ukiah

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49 miles away

Penngrove

32 miles away

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Winters

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Suisun City

47 miles away

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19 miles away

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29 miles away

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Lower Lake

11 miles away

Online Events

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How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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Thursday • 8:00 AM EDT

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Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

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

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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How To Be Kind To Yourself - Shahroo Izadi primary image

How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg primary image

(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

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Witch hunts and real lives primary image

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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

Thu, Nov 5 • 1:00 PM GMT

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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.