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It's the FIRST CLASSIC CARS & COFFEE CRUISE-IN OF 2026! You'll have the Winter Farmers Market, the Olde Towne Antique & Flea Market, unique Valentine's Day gift opportunities, and lots of food and small business discounts for classic car drivers! Bring the better half!* IT'S A CLASSIC CRUISE-IN ... AND MORE! Bring the entire family and enjoy all there is to see and do in Olde Towne. FREE coffee for classic car drivers from Serenity's Oasis, FREE up-front VIP parking for classics, antiques, hot rods, street rods, muscle cars. When you arrive, we'll hand you a growing list of DISCOUNTS FOR CLASSIC CAR DRIVERS & CREW! Gift shop and restaurant discounts up to 20% for cruise-in drivers! Over 60 vendors, tons of food, farm produce, artwork, and artisanal goods on display. Costumed characters, historic re-enactors, live music, friendly people! We'll also have our unique small shops and restaurants open throughout Olde Towne to welcome you.
100% FREE! NO REGISTRATION FEE - IF ANYONE TRIES TO GET YOU TO PRE-REGISTER OR PAY, IT'S A SCAMMER, BLOCK THEM!
Don't want to sit in a boring empty parking lot? Don't want to be trapped at a crowded, "must-stay-all-day" car show? Want to go to a car gathering where there is stuff for your significant other to do? Got a classic ride? Then join us on Saturday from 10:00AM-1:30PM! Also, grab some ice cream from our on-site shop, owned & run by teenage "girl boss" entrepreneurs! Grab some food and sit in the brick courtyard and listen to live music! Great spot to bring the spouse and family, always something different, and very welcoming! Just flag down anyone in a yellow traffic safety vest, and our military volunteers will guide you to a free prime spot. 😀
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Event Venue & Nearby Stays
493 Court Street, Portsmouth VA 23704, 493 Court St, Portsmouth, VA 23704-3603, United States
Concerts, fests, parties, meetups - all the happenings, one place.
