Share the news!

THE FINE ARTS FESTIVAL CELEBRATES 52 YEARS THIS MEMORIAL DAY WEEKEND

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.

THE FINE ARTS FESTIVAL CELEBRATES 52 YEARS THIS MEMORIAL DAY WEEKEND
By Cathy Ithier December 26, 2025
Snowy weather calls for adventure. Fairfield After Dark rounds up the best ski resorts near Connecticut for winter fun.
December 24, 2025
Michael Jackson’s iconic hits come alive with Who’s Bad, the ultimate MJ tribute, live at The Palace Theatre Stamford on January 16.
By FAD STAFF December 24, 2025
Experience A Kenny Chesney Tribute with Pirate Flag live at The Palace Theatre Stamford on January 17. High-energy country hits—tickets on sale now.
By Cathy Ithier December 19, 2025
GRAMMY winners The Band Perry perform Jan 10 at The Palace Theatre Stamford, joined by rising artist Stephanie Ryann.
By FAD STAFF December 18, 2025
Stamford, CT - Looking for a fun, family-friendly event in Stamford this holiday season? The Canine Stars is bringing its high-energy stunt dog show to The Palace Theatre Stamford on Sunday, December 28 , and Fairfield After Dark is giving one lucky family the chance to win a free family four-pack of tickets . The Canine Stars is a nationally touring, fan-favorite live show featuring talented rescue dogs performing incredible stunts, agility tricks, and crowd-pleasing routines. This interactive performance is perfect for kids, parents, and dog lovers of all ages, making it one of the best family events in Fairfield County this winter. Before the show, ticket holders can attend a special pre-show dog adoption event from 1:00–3:00 PM , where families can meet adoptable dogs and connect with local rescue organizations. It’s a heartwarming way to support animal adoption while enjoying a memorable day out. Fairfield After Dark has secured four tickets for one lucky family to attend this exciting live performance at The Palace Theatre Stamford. 👉 To enter to win, click the link: ENTER TO WIN Prefer not to wait? Tickets to Canine Stars at The Palace Theatre Stamford are available now and are expected to sell quickly. Whether you enter the giveaway or purchase tickets, this is a must-see holiday event for families in Fairfield County.
By Cathy Ithier December 17, 2025
All your holiday shopping is done—now it’s time to relax and enjoy the week ahead. Whether you’re in the mood for a lively Trivia Night, a Sip & Learn French experience, or a night of laugh-out-loud comedy, Fairfield After Dark has you covered. We’ve curated our weekly happenings to keep you entertained through Sunday, with something happening every day in and around Fairfield County. Take a look at what’s on tap and start planning your week of fun. And Enter To Win 2 Tickets to see StevieMac: A Fleetwood Mac and Stevie Nicks Experience here. Wednesday 17th,2025 Bridgeport: Trivia Night - Hub & Spoke, Black Rock(7:30pm-9:30pm) Fairfield: Trivia - Flipside Burgers & Bar, Fairfield(7pm-9pm) Fairfield: Live music with The Lamb Jam at The Seagrape Fairfield(8:30pm) Milford: Trivia Night - Flipside Burgers & Bar, Milford(7pm) Milford: Trivia Night at Tribus Beer Co.(7:30pm-9:30pm) Milford: Laugh Tracks Standup Comedy – John Bennett(8pm-10pm) Newtown: Sip n Learn French Class at Aquila's Nest Vineyards(6pm) Newtown: Sips & Sparks Singles Mixer at Aquila's Nest Vineyards(7pm) Newtown: Wednesday Night Trivia at Reverie Brewing(7pm) Stratford: WEDNESDAY NIGHT TRIVIA AT AREA TWO(6:30pm) Stratford: Open Mic Night at Joey C's(7pm-10pm) Stamford: Comedians Alex Pavone, Chris Scopo, Tocarra Elise, Jason Choi at New York Comedy Club Stamford (7:00pm) Stamford: Trivia with MC JHype - Tiernan's, Stamford(7pm-9pm) Stamford: Open Mic Night at Half Full Brewery(7pm-9pm) Thursday 18th,2025 Bethel: Trivia Night at Broken Symmetry(7pm) Bridgeport: Hurley Hour LIVE at Bryac(6pm) Bridgeport: Vicky & Adam LIVE at The Castle Black Rock(7pm-10pm) Bridgeport: Party With Friends at Bryac(9pm) Danbury: Line Dancing LIVE at Elicit - Danbury(7pm) Danbury: Thursday Open Jam with Fuzz LIVE at Sugar Hollow Taproom(8pm) Fairfield: Tangled Vine LIVE at The Sinclair(8:30pm) Milford: Young Dan & Jumpin Johnny LIVE at Cafe Atlantique(5pm-8pm) Newtown: Chocolate Fondue Dip & Sip at Aquila's Nest Vineyards(6pm) Newtown: Trivia Night at Newsylum Brewing Co(6:30pm) Norwalk: Live music with STEVEN KEITH!(5:30pm-8:30pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Old Greenwich: Mojo LIVE at BOSCO's Bar & Grill(9pm-12am) Ridgefield: Chris Cavaliere LIVE at Nod Hill Brewery(6:30pm) Rowayton: Henry Jones LIVE at Sails American Grill(6pm-9pm) Sherman: Open Mic Night - JCC in Sherman(6:30pm-8:45pm) Shelton: Happy Sally LIVE at Pier 131(7pm-10pm) Stratford: Jukebox Bingo(6:30pm-9pm) Westport: Live music with Billy Genuario(9pm) Friday 19th,2025 Bethel: IRIS LIES LIVE at Notch 8(8pm) Bridgeport: Style Acoustic LIVE at The Castle Black Rock(8pm-11pm) Bridgeport: Otis & The Hurricanes LIVE at Bryac(9:30pm) Danbury: Snake Dog LIVE at Sugar Hollow Taproom(8:30pm) Danbury: DJ SKATE FRIDAYS at Danbury Arena(8:30pm-10:30pm) Danbury: Melodus LIVE at Elicit - Danbury(9pm) Danbury: Sex & Candy LIVE at Elicit - Danbury(9pm) Danbury: DJ Roc LIVE at Elicit - Danbury(10pm) Fairfield: Hawkins French LIVE at Elicit Fairfield(9pm) New Milford: Pimpinella LIVE at Houstatonic River Brewing(7pm-10pm) Milford: Ode to Rosie LIVE at Cafe Atlantique(6:30pm-9:30pm) Newtown: Johnny Chapman - LIVE at Newsylum Brewing Co.(6pm-9pm) Newtown: Scratch LIVE at Reverie Brewing(6pm-9pm) Newtown: Mike Super Magic & Illusion at Edmond Town Hall(7pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: Jukebox Radio LIVE at 314 Beeer Garden(7:30pm-10:30pm) Old Greenwich: Chasing Romeo LIVE at BOSCO's Bar & Grill(9pm-12am) Port Chester, NY: Pigeons Playing Ping Pong with Spafford LIVE at Capitol Theatre - Port Chester, NY(7:30pm) Ridgefield: Traditional Irish Session LIVE at Nod Hill Brewery(6pm) Rowayton: Billy G and Friends LIVE at Sails American Grill(9pm-12am) Sherman: MahJongg Fridays LIVE at JCC in Sherman(12pm) Stamford: Comedian Michael Blaustein at New York Comedy Club(7pm-9:30pm) Stamford: Dive Bar Confessional LIVE at Bobby V's Stamford(7pm-10pm) Stamford: StevieMac Fleetwood Mac Tribute at The Palace Theatre Stamford(8pm ) Stamford: Captain Obvious LIVE at Third Place by Half Full Brewery(8pm-10pm) Stamford: Bad Management LIVE at Tiernan's Bar(9:30pm) Stratford: Flannel Clad Masses LIVE at Windmill Tavern(8pm) Stratford: Latin Night Afinke Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Westport: Green Eyed Lady LIVE at Black Duck Cafe(9:30pm) Saturday 20th,2025 Bethel: SETH ASAM LIVE at Shakedown Street Eats(6:30pm) Bethel: JUNK LIVE at Notch 8(8pm) Bridgeport: Live Music + Poetry at “Corridor for Ghosts and Heralds” Exhibition(7pm-9pm) Bridgeport: Greater Bridgeport Symphony Presents Holiday Quintessence December 20 at The Klein Memorial Auditorium in Bridgeport, CT(7:30pm-10pm) Bridgeport: Ruff Dogs LIVE at The Castle Black Rock(8pm-11pm) Bridgeport: Grateful Ghost LIVE at Bryac(10pm) Danbury: Sugar House Winter Show w/ Chowdah Music LIVE at Sugar Hollow Taproom(7:30pm) Danbury: FDR DRIVE LIVE at Molly Darcy(10pm) Darien: FAN FICTION LIVE at The Goose(9pm-12am) Fairfield: Beggars & Choosers LIVE at Elicit Fairfield(9pm) Milford: Cintia Maio/ Sydney DiStefano (DOUBLE HEADER) LIVE at Cafe Atlantique(6:30pm-9:30pm) New Canaan: Mind the Gap LIVE at Gates Restaurant(8:30pm-11:30pm) New Milford: The Outcrops LIVE at Houstatonic River Brewing(7pm-10pm) Newtown: Shawn Taylor LIVE at Aquila's Nest Vineyards(1pm-4pm) Newtown: Silent Disco Ugly Sweater Party at Aquila's Nest Vineyards(6pm) Newtown: Mike & Ike LIVE at Newsylum Brewing Co.(3pm-6pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Norwalk: For Legal Reasons LIVE at 314 Beeer Garden(7:30pm-10:30pm) Norwalk: Live Music Every Saturday(10pm) Old Greenwich: Kovac Brothers Winter Fest LIVE at BOSCO's Bar & Grill(9pm-12am) Port Chester, NY: Pigeons Playing Ping Pong with Great Blue LIVE at Capitol Theatre - Port Chester, NY(7:30pm) Stamford: Comedian Michael Blaustein at New York Comedy Club(7pm-9:30pm) Stamford: Little River Band at The Palace Stamford(8pm) Stamford: The Proper Villains LIVE at Tiernan's Bar(9:30pm) Stratford: Bad Mannerz LIVE at Windmill Tavern(8pm) Stratford: Bernadettes Christmas Party LIVE at Joey C’s Boathouse(9pm-12am) Westport: Shell Shockt LIVE at Black Duck Cafe(9:30pm) Sunday 21st,2025 Bethel: BRUNCH with LORRAINE MCGUIRE LIVE at Shakedown Street Eats(11am) Bridgeport: Stephen Capalbo LIVE at The Castle Black Rock(5pm-8pm) Bridgeport: The Red Planet LIVE at Bryac(6pm) Milford: Dan Watson LIVE at Dockside Brewery(2pm-5pm) New Milford: Seth Adam LIVE at Houstatonic River Brewing(4pm-7pm) Newtown: Local Cheese & Wine Pairing at Aquila's Nest Vineyards(12pm) Newtown: Jailhouse LIVE at Reverie Brewing(2pm-5pm) Newtown: Comedy Night at Aquila's Nest Vineyards(5pm) Newtown: An Irish Christmas with Andy Cooney comes to Edmond Town Hall(7pm-9pm) Norwalk: Jazz Brunch LIVE at Odeen's Restaurant(12pm) Norwalk: Live Himalayan Music at Himalaya SoNo(6:30pm-8:30pm) Shelton: DJ Revuelo LIVE at Pier 131(11:30am-3:30pm) Stamford: Comedian Michael Blaustein at New York Comedy Club (NEW SHOW ADDED)(4:30pm)
More Posts