Things To Do This Week in and Around Fairfield County, CT

Week of Wednesday, June 4 – Sunday, June 8, 2025 

Another stacked week of concerts, comedy, outdoor events, car shows, family festivals, and more — all happening in and around Fairfield County! Whether you’re craving local live music, a day of food & fun, or something totally unexpected (Silent Disco at Aquila's Nest  Vineyards, anyone?) We have your plans right here.

This week’s guide is made possible by  Edmond Town Hall in Newtown.

Edmond Town Hall's featured event this week:

Jason Salmon featuring Joe Gerics hits the Edmond Town Hall stage Saturday, June 7 (8–10 PM)! Don’t miss this hilarious stand-up show. Plus, the ETH Drive-In Movie Series kicks off on Friday and Saturday with E.T. under the stars. 

👉 Get Your Comedy Tickets | Drive-In Movie Info 

🎤 Wednesday, June 4

• 🎷 Piermont, NY: Peruvian Jazz with Hector Morales Trio at OTTO'S (6-9pm).
• 😂 Stamford: Comedy Showcase featuring KP Anderson, Maggie Lalley, Colin Pasquarella, Dan Kalwhite at New York Comedy Club Stamford (7pm)

🎶 Thursday, June 5

• 🍽️ Danbury: CityCenter Chow-Down 2025 – More Info (11:30 AM)
• 🎸 Fairfield: The Barons at Sherman Green Gazebo (6:30–8 PM)
• 🎵 Greenwich: Joe Calzone’s Mad Dog Redux at Music on the Great Lawn (6:30–8 PM)
• 🍷 Newtown: Small Business Speed Networking at Aquila’s Nest Vineyards (6–9 PM)
• 🎺 Piermont, NY: Jazz Thursday with Antonine Drye & Kevin Lovejoy at OTTO'S  (6–9 PM)
• 🎤 Ridgefield: Honey Island Swamp Band at Ballard Park (7 PM)
• 😂 Stamford: Comedy Night with Kaneez Surka, Jared Waters & more at New York Comedy Club Stamford (7 PM)
• 🌟 Westport: Taste of Westport 2025: A Night at Studio 54 at The Inn at Longshore

🎸 Friday, June 6

• 🎶 Bethlehem: Southern Voice Band at March Farm’s Summer Concerts (6–8 PM)
• 🎤 Bridgeport: Gab Kallay at Port 5 (5–8:30 PM)
• 🎼 Brookfield: Sweet Redemption at Brookfield Concerts in the Park (6:30 PM)
• ☘️ Danbury: Mighty Ploughboys at CityCenter Danbury (7–9:30 PM)
• 🥁 Milford: Shot Down at Fowler Field’s Fridays After Five Concert (6 PM)
• 🦞 Newtown: Lobster Fest at Sandy Hook Volunteer Fire & Rescue (5–9 PM)
• 🎸 Newtown: Christopher Newell LIVE at Aquila’s Nest Vineyards (5:30–8:30 PM)
• 🍷 Newtown: Sunset Wine Pairing Dinner at Aquila’s Nest Vineyards (6:30 PM)
• 📽️ Newtown: **ETH DRIVE-IN: E.T. ** at Edmond Town Hall (9 PM)
• 🎶 Norwalk: Jed Luckless LIVE at SONO 1420 (6–9 PM)
• 🎺 Stamford: Swing into the Park with Fairfield Counts at Mill River Park (7–9 PM)
• 😂 Stamford: Des Bishop: The Des Bishop Work Experience (4 showtimes) at New York Comedy Club Stamford
• 🎼 Wilton: Choral Concert at St. Matthew’s Episcopal Church (8–9 PM)
• 🎻 Westport: Dan Tressler & Friends at Music on Church Lane (6–9 PM)

🥳 Saturday, June 7

• 🐯 Bridgeport: Wild Wine, Beer & Food Safari Party at Connecticut’s Beardsley Zoo (6 PM)
• 🥁 Fairfield: Silver Steel Student Band at Sherman Green Gazebo (6:30–8 PM)
• 🏹 Harwinton: Robin Hood’s Medieval Faire® – Info & Tickets (10:30 AM–6 PM)
• 🎶 Newtown: Parker's Tangent at Aquila’s Nest Vineyards (2:30–5:30 PM)
• 👑 Newtown: Decades Drag Music Show at Aquila’s Nest Vineyards (7 PM)
• 😂 Newtown: Stand-Up Comedy with Jason Salmon ft. Joe Gerics at Edmond Town Hall (8–10 PM)
• 📽️ Newtown: **ETH DRIVE-IN: E.T. ** at Edmond Town Hall (9 PM)
• 🦞 Sandy Hook: Lobster Fest 2025 at Sandy Hook Volunteer Fire & Rescue (4 PM)
• 😂 Stamford: Early Bird Comedy at  New York Comedy Club Stamford  (4:30 PM)
• 😂 Stamford: Des Bishop continues (4 showtimes) at New York Comedy Club Stamford
• 🎤 Westport: Acoustic Elixir at Music on Church Lane (6–9 PM)

🍓 Sunday, June 8

• 🎸 Bridgeport: Black Rock Day w/ Simple Jim at Port 5 (3 PM)
• 🚘 Fairfield: Fairfield's 9th Annual Car Show at Ludlowe High School (9 AM–3 PM)
• 🎶 Fairfield: Herman & Company at Sherman Green Gazebo (6:30–8 PM)
• 🧒 Greenwich: Jumpin’ Jams @ Tides + Tunes (10 AM)
• 🎸 Greenwich: The Danned @ Tides + Tunes (4 PM)
• 🏹 Harwinton: Robin Hood’s Medieval Faire® – Tickets (10:30 AM–6 PM)
• 🏴‍☠️ Milford: 23rd Annual Pirate’s Day – Downtown Milford CT (8 AM–2 PM)
• 🍓 Mystic: Strawberry Festival at Olde Mistick Village (11 AM–6 PM)
• 🎪New Britain: Little Poland Festival – More Info (8:30 AM–7 PM)
• 🎶 Newtown: Valerie Rose at Aquila’s Nest Vineyards (2–5 PM)
• 🎧 Newtown: Silent Disco Spring Party at Aquila’s Nest Vineyards (6 PM)
• 🎤Norwalk: Flag Day with Fairfield Counts at Norwalk Green Summer Concerts (5–6:30 PM)
• 🎹 Piermont, NY: Sunday Piano Brunch with Kevin Lovejoy at OTTO'S (12–3 PM)
• 🎸 Shelton: Canyon at Jones Winery (2–4 PM)
• 🎤 Sherman: Unbroken Glass at Sherman Summer Concert Series (4–7 PM)
• 😂 Stamford: Comedy Night at New York Comedy Club Stamford  (7 PM)
• 🎹 Trumbull: Pipe Organ Recital by Daniel Colaner at St. Theresa RC Church (4:30–5:30 PM)
• 🎪 Wilton: Georgetown Day – Event Info (12–5:30 PM)