Best events in
Oakville

Looking for events or things to do in Oakville, CT? This area, which includes the broader town of Watertown, has a relaxed, community-focused feel centered on local breweries, wineries, and a classic New England town center. The social scene becomes more lively during warmer months with popular outdoor festivals and concert series that draw families from across the region.

The Watertown town center along Main Street serves as a hub for community gatherings, including the periodic Night Out on Main Street festival.
Local theater productions can be found at the Phoenix Stage Company, an all-volunteer community playhouse located right in Oakville.
Hawk Ridge Winery and The Sunset Grille at the Crestbrook Golf Course are popular spots for enjoying scenic views alongside live music performances.

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Events near Oakville

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C^nty Advice Live!

Tomorrow • 7:00 PM

Upline

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Speed Dating Ages 50-65 in Newtown, CT at Aquila's Nest Vineyards

Friday • 7:00 PM

Aquila's Nest Vineyards

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Starry, Starry Night - an Early Autumn Evening in the Litchfield Hills

Sat, Oct 3 • 5:00 PM

Camp Washington, Kenyon Road, Lakeside, CT, USA

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Fall Themed Beaded Tree of Life Suncatcher Workshop

Wed, Oct 7 • 5:30 PM

The Bristol Bazaar

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11TH ANNUAL OKTOBERFEST GOLF TOURNAMENT

Sat, Oct 10 • 12:00 PM

The Golf Club at Oxford Greens

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Moonlight Masquerade Dracula Ball

Sat, Oct 24 • 8:00 PM

Torrington Elks Lodge #372

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The Living Tombstone: The Multiplayer Tour

Sat, Oct 24 • 8:00 PM

College Street Music Hall

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The Mobile Pub 10th Anniversary Event

Sun, Oct 25 • 12:00 PM

Woodtick Recreation Area

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C^nty Advice Live!

Tomorrow • 7:00 PM

Upline

Check ticket price on event

Speed Dating Ages 50-65 in Newtown, CT at Aquila's Nest Vineyards

Friday • 7:00 PM

Aquila's Nest Vineyards

Check ticket price on event

Starry, Starry Night - an Early Autumn Evening in the Litchfield Hills

Sat, Oct 3 • 5:00 PM

Camp Washington, Kenyon Road, Lakeside, CT, USA

Check ticket price on event

Fall Themed Beaded Tree of Life Suncatcher Workshop

Wed, Oct 7 • 5:30 PM

The Bristol Bazaar

Check ticket price on event

11TH ANNUAL OKTOBERFEST GOLF TOURNAMENT

Sat, Oct 10 • 12:00 PM

The Golf Club at Oxford Greens

Check ticket price on event

Moonlight Masquerade Dracula Ball

Sat, Oct 24 • 8:00 PM

Torrington Elks Lodge #372

Check ticket price on event

The Living Tombstone: The Multiplayer Tour

Sat, Oct 24 • 8:00 PM

College Street Music Hall

Check ticket price on event

The Mobile Pub 10th Anniversary Event

Sun, Oct 25 • 12:00 PM

Woodtick Recreation Area

Check ticket price on event

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Online Events

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Today • 10:00 AM PDT

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Online Group Reading - September 27

Today • 8:00 PM ADT

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Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

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Black Girl Book Fair! Spooky Edition

Saturday • 12:00 AM CDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Today • 10:00 AM PDT

Check ticket price on event

Online Group Reading - September 27

Today • 8:00 PM ADT

Check ticket price on event

Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

Check ticket price on event

Black Girl Book Fair! Spooky Edition

Saturday • 12:00 AM CDT

Check ticket price on event

Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

Check ticket price on event

A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Oakville

Where can I find live music events in the Oakville area?

Hawk Ridge Winery is a popular destination for live music with scenic vineyard views. The Sunset Grille and The Jameson Pub in Watertown also regularly host performers, creating a relaxed and social atmosphere for an evening out.

Are there any free events for families in Watertown?

The Watertown Summer Concert Series offers free outdoor performances at Veterans' Memorial Park. This recurring event is a great way for families to enjoy music together, and the park also hosts the annual Watertown Fall Festival.

What are some food and drink events in the area?

Lasting Brass Brewing Co. in Oakville provides a rustic setting for craft beer and food truck events. For a different vibe, Hawk Ridge Winery offers wine tastings, and the Night Out on Main Street event features various food vendors.

What is the nightlife scene like in Oakville and Watertown?

The local nightlife is generally relaxed, centered on pubs and wineries with live music. Establishments like The Jameson Pub or Hawk Ridge Winery offer cozy evening entertainment. For more extensive late-night options, many locals head to nearby Waterbury.

How can a couple spend a nice evening out in the area?

A performance at the Phoenix Stage Company community theater offers a classic date night experience. Alternatively, sharing a wine tasting at Hawk Ridge Winery or enjoying a casual evening at Lasting Brass Brewing Co. are also popular choices.

Are there outdoor events happening around Watertown?

Veterans' Memorial Park is the main hub for major outdoor community events in Watertown. It's home to the annual Watertown Fall Festival and the Watertown Summer Concert Series. Night Out on Main Street also transforms downtown into an open-air event.

What's the best way to experience the local culture in Watertown?

Strolling down Main Street gives a great sense of the local New England charm and community focus. The Night Out on Main Street festival is a signature event that brings together local artists, food vendors, and music right in the heart of town.

Does Oakville host any local arts or theater events?

The Phoenix Stage Company is the heart of Oakville's local theater scene. This all-volunteer community theater presents a variety of shows, providing an intimate setting for performing arts events and showcasing local talent throughout its season.

Events near Oakville

C^nty Advice Live!

Speed Dating Ages 50-65 in Newtown, CT at Aquila's Nest Vineyards

Starry, Starry Night - an Early Autumn Evening in the Litchfield Hills

Fall Themed Beaded Tree of Life Suncatcher Workshop

11TH ANNUAL OKTOBERFEST GOLF TOURNAMENT

Moonlight Masquerade Dracula Ball

The Living Tombstone: The Multiplayer Tour

The Mobile Pub 10th Anniversary Event

C^nty Advice Live!

Speed Dating Ages 50-65 in Newtown, CT at Aquila's Nest Vineyards

Starry, Starry Night - an Early Autumn Evening in the Litchfield Hills

Fall Themed Beaded Tree of Life Suncatcher Workshop

11TH ANNUAL OKTOBERFEST GOLF TOURNAMENT

Moonlight Masquerade Dracula Ball

The Living Tombstone: The Multiplayer Tour

The Mobile Pub 10th Anniversary Event

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Nearby cities

Hartford

New Haven

Stamford

Bridgeport

Norwalk

Danbury

Springfield

West Hartford

Bristol

Beacon

Middletown

Westport

Westfield

Port Jefferson

Manchester

Poughkeepsie

Holyoke

Newington

Milford

Waterbury

Cos Cob

Carmel Hamlet

New Britain

Bethel

Agawam Town

Newburgh

Mount Kisco

Meriden

Wethersfield

North Haven

Hartford

New Haven

Stamford

Bridgeport

Norwalk

Danbury

Springfield

West Hartford

Bristol

Beacon

Middletown

Westport

Westfield

Port Jefferson

Manchester

Poughkeepsie

Holyoke

Newington

Milford

Waterbury

Cos Cob

Carmel Hamlet

New Britain

Bethel

Agawam Town

Newburgh

Mount Kisco

Meriden

Wethersfield

North Haven