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A Westport Women's Club Tradition - Yankee Doodle Fair Returns JUNE 16 – 19, 2022
YANKEE DOODLE FAIR RETURNS JUNE 16 – 19
On Father’s Day Weekend, “kids of all ages” will gather at the Westport Woman’s Club (44 Imperial Avenue, Westport, CT) to enjoy one of the town’s oldest and best-loved family events, The Westport Woman’s Club’s YANKEE DOODLE FAIR. This year’s family fair opens Thursday, June 16 (6pm – 10pm) and continues Friday, June 17 (6pm – 10pm), Saturday, June 18 (1pm – 10pm) and Sunday, June 19 (1pm – 5pm).
The Yankee Doodle Fair will once again feature carnival rides and games. Returning are the ever-popular Carousel, Flying Dumbo, Dizzy Dragon, Frog Hopper, Scrambler, Cliff Hanger, Zero Gravity, Expo Wheel, among others. Pay-one-price unlimited ride wristbands will be available all days of the fair. Our youngest visitors will be excited to know that sand art is available at the fair again this year. Inside the air-conditioned Bedford Hall, our Gourmet Group will hold their highly anticipated bake sale featuring home-made baked goods sure to please every sweet tooth.
Entertainment at this year’s Yankee Doodle Fair will include: SWEETCAKE MOUNTAIN, an all-acoustic country/bluegrass band performing Saturday (4pm - 6pm); HAWKNS, a Connecticut Classic Rock Pop Band performing Friday (7:45pm – 9:45pm) and Saturday (7pm - 9pm). In addition, WESTPORT VOLUNTER EMS will have one of their ambulances at the Fair on Saturday afternoon to share with fairgoers; this spring the Westport Woman’s Club granted $300,000 to WVEMS to purchase a new ambulance to service the community.
Throughout the fair, you will have an opportunity to buy tickets for the Yankee Doodle Fair raffle prizes. First prize is $1000, second prize is $500, and third prize is a rose gold and diamond necklace valued at $650. In addition, our Yankee Doodle Fair’s “Take a Chance” tent is returning this year with a wide variety of prizes, many donated by Westport’s generous merchants and restaurants. “Take a Chance” prizes will be available for viewing throughout the fair under a tent on the fair’s upper level, where you can buy tickets enter to win “Take a Chance” prizes. All winning raffle and “Take a Chance” tickets will be drawn at the end of the fair on Sunday, Father’s Day. It is not necessary for winners to be present to claim their prizes.
At the Yankee Doodle Food Court, fellow non-profit WESTPORT EXCHANGE CLUB will feature a selection of hamburgers, hot dogs, etc., as well as wine and beer to customers of legal age. GRECIAN DELIGHTS will be offering Greek favorites, gyros, souvlaki, and shish kabob. Skip’s vintage GOOD HUMOR truck will have ice cream treats for every taste, and THE ULTIMATE WAFFLE will be selling ice cream waffle treats throughout the fair. In addition, members of the Westport Woman’s Club will be selling cold beverages and bottled water, with proceeds benefitting WWC community service grants and need-based scholarships for Staples High School seniors.
No dogs are permitted on the grounds during the fair.
The Westport Woman’s Club, organized in 1907, is a non-profit philanthropic organization dedicated to volunteerism and the raising of funds in support of the educational, charitable, cultural, and public health services in Westport and surrounding towns. You do not have to be a Westport Resident to join The Westport Woman’s Club. For more information or to join this historic philanthropic organization, visit www.westportwomansclub.org or call the WWC office at 203-227-4240.
Memorial Day Weekend marks the unofficial start of summer—and there’s no better place to celebrate than right here in Connecticut. From May 24–26, the state comes alive with a jam-packed lineup of festivals, carnivals, parades, and concerts offering something for everyone. We’re excited to announce that our very first sponsor for the Things to Do in and around Fairfield County series is the Westport Downtown Association (WDA) , proud presenter of the 52nd Annual Westport Fine Arts Festival happening May 24 & 25, 2025. We're honored to be named a media sponsor for this beloved event, which brings thousands of visitors to downtown Westport for a weekend filled with outstanding fine art, live music, family activities, and vibrant local culture. The WDA is a nonprofit organization committed to promoting the economic and cultural vitality of downtown Westport. Their mission is to enrich the downtown experience through engaging community events, beautification efforts, and charitable support for local nonprofits—all to ensure Westport remains a thriving and welcoming destination. Beyond Westport, towns across Connecticut are kicking off summer in style. From the medieval magic of Robin Hood’s Faire to the mouthwatering flavors of your favorite food trucks at local carnivals and festivals, there's no shortage of fun. Fairfield County communities are joining the celebration with patriotic parades and family-friendly fairs, while summer concert series bring music to every corner—like Stamford’s high-energy shows at Mill River Park , Fairfield’s classic performances at Sherman Green Gazebo , Norwalk’s laid-back Calf Pasture Beach concerts, and Ridgefield’s treasured CHIRP series at Ballard Park . Whether you’re dancing under the stars, riding the Ferris wheel, or savoring local eats, Memorial Day Weekend is the perfect time to connect with your community, enjoy great music, and embrace the great outdoors in the Nutmeg State. Please note: Event details are subject to change due to weather. Admission is free unless otherwise noted. Check out our Daily Roundup of fun things to do in and around Fairfield County. Wednesday, May 21 Newtown: Aquila’s Nest Vineyards – Funk, R&B, Rock, ‘60s - ‘80s (6:30pm-9:30pm) Stamford: Comedian Mike Cannon at New York Comedy Club Stamford (7pm) Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) Piermont, NY: Latin Wednesday with Charanga Duo at OTTOS (6-9pm) Thursday, May 22 Danbury: City Center Chow-Down (11:30am – 1:30pm) Fairfield: Fairfield Parks & Rec – The Paula G Band at the Sherman Green Gazebo (6:30-8pm) Fairfield: Comedian Sean Patton on StageOne at FTC (8pm) Greenwich: Greenwich Historical Society – Jazz Music with Richie G (6:30pm-8pm) Newtown: Aquila’s Nest Vineyards – Kara Colvin LIVE (5:30-8:30pm) Piermont, NY: Jazz Thursday with Scott Robinson & Kevin Lovejoy at OTTOS (6-9pm) Stamford: Comedian Marcella Arguello at New York Comedy Club Stamford (7pm) Friday, May 23 Fairfield: Brian Dolzani Band W/ North County Trio LIVE at StageOne in FTC (8pm) Milford: Fridays After Five at Fowler Field – Kathy Thompson Band (6pm) Norwalk: SONO 1420 – Acoustic SONO Music Series with Bittersweet Descent (6-9pm) Newtown: Aquila’s Nest Vineyards – Don Lowe LIVE (5:30-8:30pm) Stamford: Comedian Angelo Colina at New York Comedy Club Stamford (8pm) Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) Saturday, May 24 – ( Westport Fine Arts Festival (10am-5pm) Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) Fairfield: Fairfield Park & Rec – Out on Bail at Sherman Green Gazebo (6:30-8:30pm) Greenwich: Greenwich Town Party with Alanis Morissette (10am-10pm) Hawthorne: Robin Hood's Medieval Faire (10:30am-6pm) Newtown: Aquila’s Nest Vineyards – The Barn Rats (2:30pm-5:30pm) Newtown: Aquila’s Nest Vineyards – Comedy Night w/ Regina DeCicco (7-9pm) Redding: Redding Memorial Day Parade (12pm) Redding: Redding Memorial Day Picnic (1-5pm) Sherman: Memorial Day Weekend Barn Sale at Sherman Historical Society (9am-4pm) Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) Westport: Westport's Kickoff to Summer at Compo Beach (11am-3pm) Westport: Westport Fine Arts Festival (10am – 5pm) Sunday, May 25 - Westport Fine Arts Festival (10am-5pm) Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) BrookField: Memorial Day Parade (2pm) Fairfield: Dom & Nick Trio at Sherman Green Gazebo (6:30-8pm) Hawthorne: Robin Hood's Medieval Faire (10:30am-6pm) Newtown: Aquila’s Nest Vineyards – On the Road Again (2pm-5pm) Newtown: Fleetwood Mac Tribute Show at Aquila’s Nest Vineyards (6-8pm) Piermont, NY: Savor Sunday Brunch & Live Piano w/ Kevin Lovejoy at OTTOS (12PN-3PM) Sherman: Memorial Day Weekend Barn Sale at Sherman Historical Society (9am-4pm) Stamford: Comedy Jackpot Mic at New York Comedy Club Stamford (4pm) Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) Westport: Westport Fine Arts Festival (10am – 5pm) Monday, May 26 Bridgeport: Chris Rowlands Live at Connecticut's Beardsley Zoo (10am) Darien: Darien Memorial Day Parade (10am) Fairfield: Fairfield Memorial Day Parade (10am) Greenwich: Jim Fixx Memorial Day Race (10am) New Canaan: New Canaan Memorial Day Parade (9:30am) Newtown: Aquila’s Nest Vineyards – George John (1pm-4pm) Norwalk: Norwalk Memorial Day Parade (10am) Old Greenwich: Old Greenwich Memorial Day Parade (10am) Ridgefield: Ridgefield Memorial Day Parade (11:30am) Trumbull: Trumbull Memorial Day Parade (10am) Westbrook: Spring Carnival at Westbrook Outlets (1-6pm) Westport: Westport Memorial Day Parade (9am)
Comedy lovers, mark your calendars! On Friday, June 7 at 7:30 PM , Edmond Town Hall in Newtown, CT welcomes a night of side-splitting laughter featuring two outstanding comedians— Jason Salon and Joe Gerics . 🤹♂️ Jason Salon: Absurd, Insightful, and Absolutely Hilarious Born during a freak hailstorm in Texas, Jason Salon was practically destined for the unexpected. His mom always knew something was off—and lucky for us, that "something" turned out to be comedy gold. With a style described as “like getting the best advice ever from the dumbest guy you know,” Jason blends absurdist observation with a folksy, philosophical twist that keeps audiences howling from coast to coast. Jason’s resume is packed with laugh-worthy credits: Appearances on Orange is the New Black and 30 Rock Commercials for GEICO , Toyota 4Runner , and more A roster of indie film appearances and viral internet sketches Whether he’s riffing on modern life or waxing poetic about the ridiculousness of everyday situations, Jason Salon is a comedic force you won’t want to miss. 🎟 Featuring Joe Gerics: Connecticut’s Own Comedy Powerhouse Opening the night is Joe Gerics , a Connecticut-based comic known for his razor-sharp wit and everyman charm. Joe is a staple on the New England comedy circuit, where his quick delivery and relatable material make him an audience favorite. From parenting pitfalls to pop culture, Joe’s humor is fast, fresh, and always on point. 📍 Event Details: 🎭 Edmond Town Hall – Newtown, CT 📅 Saturday, June 7, 2025 ⏰ 7:30 PM 🎟 Tickets available now at edmondtownhall.org Don't Miss This Unforgettable Night of Stand-Up Comedy! Grab your friends, grab your tickets, and prepare to laugh until it hurts. Edmond Town Hall is your go-to destination for top-tier entertainment—and June 7 is all about Jason Salon and Joe Gerics . Be there!
Aquila’s Nest Vineyards is keeping the summer vibes alive with their wildly popular Tribute Show Series—an unforgettable lineup of iconic music, vineyard views, and epic nights under the stars. These shows sell out fast, and FairfieldAfterDark has the inside scoop (and the links!) so you can grab your tickets before they're gone. Here’s what’s coming up: 🎶 Fleetwood Mac Tribute Sunday, May 25 at 6 PM Celebrate Memorial Day Weekend with the timeless sounds of Fleetwood Mac. Get ready for hits like Dreams, Go Your Own Way, and Rhiannon under the twilight sky. 👉 Get Tickets 🌌 Pink Floyd Tribute Saturday, May 31 at 6 PM Immerse yourself in the legendary sounds of Pink Floyd. Expect lasers, atmosphere, and all the vibes of Dark Side of the Moon and The Wall. 👉 Get Tickets 🔥 Bon Jovi Tribute Friday, June 20 at 6 PM Get ready to live on a prayer! This high-energy show brings Bon Jovi’s biggest hits to the vineyard stage. 👉 Get Tickets 💋 Rolling Stones Tribute Sunday, June 22 at 6 PM You can always get what you want—especially when it’s a Rolling Stones tribute show on a summer evening. 👉 Get Tickets 🌀 Psychedelic Relics Friday, June 27 at 6 PM Take a trip through the sights and sounds of the psychedelic era with Psychedelic Relics. Groovy visuals and retro classics await. 👉 Get Tickets ☀️ Panacea Summer Party Sunday, June 29 at 6 PM Close out June with an epic summer celebration featuring Panacea and their vibrant tribute vibes. It’s more than a show—it’s a party. 👉 Get Tickets 🎟 Pro tip: These shows sell out fast, so secure your tickets now and toast the summer season in style at Aquila’s Nest Vineyards.
Acoustic SONO Music Series Heats Up with Bittersweet Descent at SONO 1420. Kick off Memorial Day Weekend in South Norwalk with a free, electrifying performance! If you’re staying local this holiday weekend, Fairfield After Dark has you covered with the perfect Friday night plan: the Acoustic SONO Music Series at SONO 1420 American Craft Distiller s . On Friday, May 23, from 6–9 PM , the series welcomes its latest featured artist — Bittersweet Descent . This genre-defying four-piece band fuses folk, punk, country, and rock into high-octane, original performances that are guaranteed to keep you moving and mesmerized. 🎶 Music, Mixology & More Now in full swing, the Acoustic SONO Music Series has brought an impressive lineup of local talent to SONO 1420 over the past few months. With its intimate vibe and top-shelf cocktails, the venue is quickly becoming a go-to Friday night destination. SONO 1420 is more than just a distillery — it’s an experience. Come early, stay late, and soak up the energy of live music, craft spirits, and community connection. Just bring your good vibes, grab a seat, and enjoy an evening of live music and elevated cocktails. 🥃 Host Your Next Party or Private Event at SONO 1420 Planning a celebration, team outing, or special gathering? SONO 1420 offers a one-of-a-kind venue in the heart of South Norwalk with everything you need to impress your guests: Capacity: Up to 45 for meetings, 100 for casual events Drinks: House-made spirits, Spacecat Brewery beer, and BYO wine Food: Charcuterie options available or bring your own caterer Add-ons: Custom whiskey bottles, distillery tours, and tastings Let the SONO 1420 team help you create an experience your guests won’t forget.
Kick off Memorial Day weekend with The Moonrise Cartel as they return to Park City Music Hall in Black Rock this Thursday, May 22 . With their newest single Set To Stun surpassing 100,000 streams on Spotify, this indie powerhouse is quickly rising through the ranks—and tickets for their shows sell fast. Led by the luminous vocals of Stephanie Harrison—often compared to Linda Ronstadt and Emmylou Harris—the band delivers a mix of emotionally raw songwriting and sonic brilliance. Co-founder Al Pascarelli brings depth with his gravel-toned voice and heartfelt lyrics, while Sean O’Reilly’s piano adds both tenderness and thunder, channeling the spirit of Tori Amos and Bruce Hornsby. Benj LeFevre on bass and Steve Tobey on drums lock in a rhythm section that is as fluid as it is powerful, completing the group’s unmistakable sound. Known for drawing fellow musicians to their shows, The Moonrise Cartel's live performances are electric, authentic, and not to be missed. Having opened for legends like Buddy Guy and Sophie B. Hawkins, they're clearly headed for bigger stages. 🎟️ Don’t wait—this show will sell out.
With over 165 juried Fine Artists, a Sesame Street Station in the children's area, music and food for the whole family to enjoy! WESTPORT, CT, MAY 24TH + 25TH – The Westport Downtown Association, Inc. is excited to present the 52nd Westport Fine Arts Festival, on Memorial Day Weekend - Saturday, May 24th, and Sunday, May 25th from 10 AM to 5 PM. This juried festival is a top twenty nationally ranked show and features the award-winning work of over 165 fine artists from across the country in 11 categories. Over 260 artists applied for 167 coveted spots at this year's festival. The artists come from 19 states, with 31 from Connecticut, and six from our hometown of Westport. We are delighted to welcome 41 new artists to the festival. The returning festival judges are Kathie Bennewitz and Miggs Burroughs. Additionally, we are delighted to introduce the Sesame Street Station for this year’s family area on Church Lane! This year's children's area is sponsored by Gault Family Companies, bringing Sesame Street to downtown Westport! Children of all ages can enjoy Facepainting by Yasmeen and themed crafts by CraftyKids Westport. Elmo and friends will be on-site Saturday and Sunday. Join them for games, dancing, limbo, and photo opportunities! Inspired by the beloved PBS educational show, this playful space celebrates creativity, diversity, and friendship. From Big Bird to big fun, it’s all happening downtown! Adults can relax and enjoy wine and beer sponsored by Aquila’s Nest Vineyards, Elicit Brewing Co., Gerard Bertrand, Hampton Water Rosé, The Grapevine, Martignetti Companies, Space Cat Brewing Company, and Two Roads Brewing Company. Popular food vendors such as Alina’s Cakes & Cookies, Goni’s Gourmet, Good Ole Boys Kettle Corn, Hoffman Bread, Los Poblanos Restaurant, Sweet Ness Bites, and LemoNate’s will be on-site to satisfy hungry appetites. Other vendors at the festival include Advanced Window Systems LLC, CY Collective, Day at the Beach, Domino Travel, Huntington Learning Center of Westport, Joli Lily, Leaf Filter, Renewal by Anderson, Students Opening Local Displays (SOLD Club), Sweet Bond, and Waxing the City Westport. Liefer Properties sponsors the artists’ awards reception at Branson Hall on Saturday evening, May 24th. We are grateful for their generosity and support of this year’s festival. Special thanks to The Aubuchon Realty Company (ARC) for generously allowing festival attendees to enjoy live music on their Elm & Main property. The Fine Arts Festival is a free event. All art will be available for purchase at various price points. The festival will have three entry points: Elm Street, Main Street, and Avery Place. Festival visitors will enjoy live music on both days in several locations on the festival's footprint. This festival is a highlight for collectors and residents of the Tri-State region, New England, and beyond. It features a premier roster of regional, national, and international fine artists exhibiting in various media categories, including painting, photography, sculpture, fiber, printmaking, mixed media, glass, ceramics, jewelry, wood, graphics, and printmaking. All artwork is available in various price ranges, themes, and styles. The Westport Fine Arts Festival would not be possible without the generous sponsorship of Gault Family Companies, Leifer Properties, Finocchio Brothers, and Videler Photography. We’re grateful to our media sponsors, 06880 Dan Woog and Fairfield After Dark, for their generous support in promoting the event and contributing to the community. The 52nd Westport Fine Arts Festival is presented and produced by The Westport Downtown Association, with Artist Direction by Sue Brown Gordon of Gordon Fine Arts. If artists have questions, they can reach Sue at fafdirector@westportdowntown.com or (518) 852-6478. On-site and sponsor positions are available. Contact Beth Meyer at events@westportdowntown.com. Press inquiries should be directed to Brian Spurr at marketing@westportdowntown.com. For more information, please go to https://westportdowntown.com/fine-arts-festival. The Westport Downtown Association (WDA) is a non-profit 501(c)(3) advocacy organization of merchants, business owners, and landlords working together to improve the commerce and culture of downtown Westport, Connecticut, for the benefit of our community and commercial constituents. In addition to supporting the maintenance and beautification of our district, the WDA runs consumer events to draw attention and visitors to the area.