Retail 360: Holiday Customer Experience

Creating Memorable Holiday Moments From the Sidewalk to the Sale


Wednesday, November 4, 2026
3:00 PM - 5:00 PM (EST)
* Registration open until 11/3/26 at 7:00 PM (EST)
Register Now
* Registration open until 11/3/26 at 7:00 PM (EST)
Southside Event Registration
Category: Education Events

November 4 | 3:00 PM - 5:00 PM
Beginning at York & Main

The holiday season brings more than increased traffic. It brings new customers, higher expectations, and an incredible opportunity to turn a seasonal visit into a lasting customer relationship.

Join us for a special, on-location Retail 360: Holiday Customer Experience, an interactive afternoon designed to help you step outside of your own business and experience retail through the eyes of a holiday shopper.

Led by Jenny Crittenden, we'll visit three distinctly different Gloucester retail businesses: York & Main, a creative collective; Up South, a traditional boutique; and Kelsick Market, a specialty market. At each stop, we'll explore how different businesses create memorable customer experiences during one of the busiest and most important shopping seasons of the year.

And this isn't a traditional presentation. We'll be learning by experiencing.

Put Yourself in Your Customer's Shoes

We'll begin our afternoon at York & Main, where guests can network, explore the space, and meet fellow local business owners before jumping into our first Holiday Customer Experience conversation.

Each attendee will receive Retail Alliance's Holiday Customer Experience Assessment, a seasonal take on our customer experience tool designed to help you look more intentionally at every step of the holiday shopping journey.

As we move through each business, we'll use the assessment to consider:

  • What does the customer see and feel before they even walk through the door?
  • What happens within the first 10 to 15 seconds?
  • Does the space make holiday shopping feel easy and enjoyable?
  • How does merchandising help customers discover the right gift?
  • What role does customer service play in reducing holiday shopping stress?
  • Are there opportunities for thoughtful recommendations and add-ons?
  • What does the checkout and farewell experience leave the customer feeling?

Three Businesses. Three Perspectives. One Customer Journey.

Stop 1: York & Main

We'll start at York & Main, a creative collective, and explore how a space featuring different makers, products, and stories can create one cohesive holiday experience. We'll look at first impressions, atmosphere, product discovery, gift inspiration, and the little details that encourage customers to stay and explore.

Stop 2: Up South

From there, we'll walk together to Up South to experience the holiday customer journey through the lens of a traditional boutique. Our conversation will focus on personalized service, gift recommendations, merchandising, ease of shopping, and ways retailers can help take the stress out of holiday shopping.

Stop 3: Kelsick Market

We'll finish the afternoon at Kelsick Market, where we'll enjoy refreshments and explore the customer experience from the perspective of a specialty market. We'll bring together what we've experienced throughout the afternoon and talk about hospitality, product discovery, gifting, convenience, checkout, and creating a final impression that gives customers a reason to return. 

You'll Leave With

By the end of the afternoon, you'll have:

  • A fresh perspective on your own holiday customer experience
  • A Holiday Customer Experience Assessment you can take back to your business
  • Real-world ideas from three very different retail environments
  • Inspiration for improving service, merchandising, gift discovery, atmosphere, and customer flow
  • Practical ideas you can implement before the height of the holiday shopping season
  • A clearer picture of how you want your customers to feel when they shop with you this holiday season 

The goal isn't to copy what another retailer is doing. It's to experience what works, think about why it works, and determine how you can translate those principles into something that feels authentic to your own business and customers.

Event Details

Date: November 4
Time: 3:00 PM - 5:00 PM
Starting Location: York & Main
Additional Stops: Up South + Kelsick Market
Format: Interactive walking Retail 360 experience
Facilitated by: Jenny Crittenden 

Please plan to arrive at York & Main a few minutes early for check-in. We will travel between the three locations together, so comfortable walking shoes are encouraged.

Space is limited for this interactive experience, so register early and join us as we take a fresh look at the holiday season through the eyes of the customer.

* Registration open until 11/3/26 at 7:00 PM (EST)
Register Now
* Registration open until 11/3/26 at 7:00 PM (EST)
Southside Event Registration

Annual Presenting Sponsor


   

For More Information:

Retail Alliance Logo 101 W Main St Suite 905
Norfolk, Virginia 23510
United States
757.466.1600