It’s officially Shoptober in Virginia’s River Realm, and there’s still time to join in on the fun! Explore Middlesex is giving away five Shoptober tickets to five lucky winners — your golden pass to exclusive shopping deals, dining discounts, and local rewards all month long.
Even if you don’t win, tickets are just $20 on Ticketleap, and they unlock access to more than 50 local businesses across Middlesex, Lancaster, and Tappahannock — all celebrating local love and early holiday shopping in style.
With two full weekends left in October, we’ve put together a perfect Shoptober itinerary to inspire your next day trip or weekend getaway in Middlesex County.
Here’s How to Enter the Giveaway
- Like the giveaway post on Facebook or Instagram
- Share it to your feed or story
- Tag four shopping buddies you’d love to bring along
We’ll select one winner and their four friends to receive tickets and plan a day of shopping, dining, and fun during Shoptober. The contest ends at 5:00PM on October 23, and the winners will be announced soon after.
Note: Winners of the Explore Middlesex Shoptober Ticket Giveaway will not be eligible for the separate $500 Chesapeake Bank grand prize drawing.
Tickets unlock exclusive deals and discounts at more than 50 local businesses across the River Realm — so we’ve mapped out one of our favorite ways to spend a Shoptober day right here in Middlesex County.
☕ Start Your Morning in Deltaville
Kick off your day at The Table at Wilton with an iced coffee and something sweet.
Shoptober ticket holders enjoy 15% off at the The Market which is full of adorable chef-curated items and ingredients— plus get a FREE Dark Chocolate Sea Salt Cookie with any purchase.
Before you leave Deltaville, swing by the Boater’s Boutique at Deltaville Yachting Center for 30% off your purchase. They’re hosting an Open House and Boat Show on October 25, making it the perfect weekend to shop, explore, and get a taste of coastal life.
🛍️ Head Up the County for More Shopping
On your way toward Urbanna, stop in at River Birch Gifts — one of Middlesex’s most beloved shopping destinations. Their beautiful store is filled with apparel, gifts, home décor, toys, and gourmet goods. During Shoptober, enjoy 10% off purchases over $100.
🍔 Spend the Afternoon in Historic Urbanna
Once you reach Urbanna, grab lunch at one of the town’s local favorites:
- The Wooden Pickle – 10% off your order
- Small Town Burger – 10% off your order
After lunch, take your time strolling Urbanna’s charming, walkable streets — a true small-town shopping haven. Be sure to pop into:
- Ballgown Barefoot – 15% Off Everything *Except Consigned Art and Jewelry
- R.S. Bristow’s – 10% Off Anything With A Crab
- Fabulous Finds Boutique – 10% Off Everything
- Urbanna Trading Company – FREE Urbanna Trading Company Koozie and 15% Off on Shirts & Sweatshirts
🍽️ End the Day with Dinner & Deals
Wrap up your Shoptober adventure with dinner at The Big Oak Café, where you’ll get 10% off your entrée just for showing your ticket.
Ready to Join the Fun?
There’s still time to experience all the excitement of Shoptober in Virginia’s River Realm!
Enter the Explore Middlesex Shoptober Giveaway by following the steps above — like the post, share it, and tag four of your favorite shopping friends — for a chance to win five Shoptober tickets and plan your very own shopping day adventure. The contest ends at 5:00PM on October 23, and the winner will be announced soon after.
Don’t want to wait? You can grab your ticket now for just $20 on Ticketleap and enjoy this Middlesex itinerary or expand your trip to explore 50+ participating businesses across the River Realm offering exclusive deals through October 31.
🎟️ Buy your ticket today and make the most of Shoptober before it’s gone!
Note: Winners of the Explore Middlesex Shoptober Ticket Giveaway will not be eligible for the separate $500 Chesapeake Bank grand prize drawing.
