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Bargains, Buzz, and Big Sales: Westport’s Annual Sidewalk Sale Returns June 27–29, 2025

Shop, Stroll, and Save: Westport’s Annual Sidewalk Sale Returns June 27–29, 2025

It’s back — and bigger than ever!
The Westport Downtown Association   is thrilled to announce the return of the Annual Sidewalk Sale, happening Friday, June 27 through Sunday, June 29. This beloved summertime tradition turns the town into a shopper’s paradise, with deep discounts, exclusive offers, and special events taking place throughout the vibrant downtown area and beyond.

From Main Street and Elm Street to Church Lane, Sconset Square, and locations all across town, local boutiques, salons, specialty shops, and national retailers are participating with can't-miss deals and sidewalk specials.

🛍️   Sidewalk Vendors & Table Promotions

(Located throughout the Downtown Sidewalk Sale Area)


🏬 Retailers Across Westport Offering Exclusive Promotions

  • Arogya Holistic Healing (131 Post Road East) — 10% off Cold Brew Tea Sachets
  • Artistex Salon & Spa (260 Post Road East) —
  • VARIS styling brushes: $25
  • VARIS hot tools: $100
  • Oribe shampoos/conditioners: 25% off
  • Oribe styling products: Buy 1, Get 1 Free
  • Valid 6/27 (9am–3pm) & 6/28 (9am–4pm)
  • Athleta (103 Main Street) — In-store promotions
  • Belev.co (131 Kings Highway, Suite M4) — 20 units of Botox for $200
  • Blossom + Stem Floral Design (1835 Post Road East) — In-store specials
  • Blue & Cream (48 Post Road East) —
  • 50% off top brands like For Love and Lemons, Zimmerman, Cami NYC
  • Graphic tees: $30
  • Aviator Nation: Up to 40% off
  • Freecity: Up to 25% off
  • Nike footwear & more in-store deals
  • Bobbles & Lace (11 Church Lane) — 15% off limited styles
  • Brooks Brothers (136 Main Street) — Almost everything 30% off + Shirts 3 for $199 (Valid 6/25–7/8)
  • Chanel (58 Main Street) — Complimentary 5-minute make-up touch-up or fragrance discovery outside, or 15-minute service inside
  • Core Burn Pilates (12 Elm Street) — Free intro class or private session + 10% off (Valid 6/28 & 6/29)
  • Courtgirl (125 Main Street) — 15% off
  • Cove Collective (26 Railroad Place) — 80% off select items
  • Cold Fusion Gelato (178 Main Street) — In-store promotions
  • Ethan Allen (627-629 Post Road East) — 25% off everything + 15% off clearance
  • Faherty (26 Main Street) — Sale on men’s and women’s apparel
  • Framebridge (123 Post Road East) — Free swag & frame raffle
  • Glowbar (33 Elm Street) — $5 off first facial (Code: GLOW5)
  • Great Stuff (68 Main Street) — Deals on jeans, tops, sweaters & more
  • Honey Pie Children's Boutique (18 Riverside Ave) —
  • Up to 60% off archive items
  • $10 & $20 baskets
  • 20% off entire store
  • Hummingbird Healing Center (57 Main St, 2nd Floor) — Free Harmonic Egg® sessions raffle + Palo Santo samples (Valid 6/28 & 6/29)
  • Jenni Kayne (15 Myrtle Avenue, Store 1) — 40% off
  • Kerri Rosenthal (181 Main Street) — Up to 75% off
  • lululemon (69 Main Street) — “We Made Too Much” markdowns
  • Madewell (155 Main Street) — 40% off all sale items
  • Marine Layer (51 Main Street) — 25% off entire store
  • Middlemarch (62 Post Road East) — 50–75% off select jewelry
  • Myr’s Designs (Online) — 50% off select items + free shipping on $100+
  • Offline by Aerie (91 Main Street) — 70% off clearance
  • Rhone (7 Main Street) — Up to 50% off Summer Sale (Valid 6/23–7/2)
  • Savvy + Grace (146 Main Street) — 50–80% off sidewalk deals
  • Scout & Molly's (283 Post Road East) — Discounted apparel & accessories
  • SHOE-INN (21 Main Street) — Up to 75% off
  • Soleil Toile (14 Post Road East) — 50–70% off lingerie & swimwear
  • Sorelle Gallery (19 Church Lane) — 15% off select original art + 20% off prints
  • SoulCycle (372 Post Road East) — In-store promotions
  • Southern Tide (33 Elm Street) — Up to 70% off markdowns
  • Splash Of Pink (275 Post Road East) — 30–50% off select items (final sale)
  • Splendid (63 Main Street) —
  • Sale from $29+, Kids from $19
  • Full price 40% off
  • Preview sale 6/26
  • Squeeze Massage (625 Post Road East) —
  • New members using promo code WP1YEAR (6/18–6/30) get a free massage credited on 9/30 (restrictions apply)
  • Stephen Kempson London (5 Post Road West) —
  • Up to 70% off men’s fashion
  • Up to 40% off women’s
  • Sweathouz (374 Post Rd E, Ste 80) — Summer membership promo + cold plunge experience
  • The Plumed Serpent (240 Post Road East) — Sample gowns 30–80% off
  • The Tailored Home (15 Myrtle Avenue) —
  • 30–50% off all showroom furniture
  • 30% off accessories
  • 50% off pillows and lighting (Valid 6/27–6/28)
  • The Toy Post (180 Post Road East) — 50% off select toys
  • The Two Oh Three (107 Post Road, Fairfield) — 15–20% off summer collection + clearance bins
  • The Westport Library (20 Jesup Road) — In-store promotions (Valid 6/28–6/29)
  • Theory (87 Main Street) — Sale items
  • unsubscribed (33 Elm Street) — Up to 70% off
  • Vince (115 Main Street) — 40% off sale items
  • Vuori (166 Main Street) — Markdowns on select items
  • West (117 Post Road East) — Up to 70% off + 20% off full-price items
  • Westport Book Shop (23 Jesup Road) —
  • $3 paperback reads
  • 2 for $5
  • 5 for $10 deals
  • Williams Sonoma (25 Church Lane) — 20% off clearance

📍 Event Information Recap


Don’t miss this weekend of community, creativity, and commerce in the heart of Fairfield County.
Come early, shop local, and leave with amazing deals and new favorites.

Photos courtesy of Videler Photography from the 2024 event.

Bargains, Buzz, and Big Sales: Westport’s Annual Sidewalk Sale Returns June 27–29, 2025

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Who’s Bad Brings the Ultimate Michael Jackson Tribute to The Palace Theatre Stamford on January 16th.

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A Kenny Chesney Tribute with Pirate Flag Comes to The Palace Theatre Stamford on January 17

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.

GRAMMY-Winning Trio The Band Perry coming to The Palace Theatre Stamford — Jan 10

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Win a Family Four-Pack to See Canine Stars at The Palace Theatre Stamford – December 28.

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.

Holiday Shopping Done? Unwind With This Week’s Best Happenings Around 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)
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