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5th Annual Roll & Stroll

Thursday, November 17 Check-in opens at 5 pm

Had your picture taken with Santa & Mrs. Claus?
Find and download your complimentary portrait* here!
You can find your Gallery # on the slip of paper you received at the Roll & Stroll.

*The free download is great for sharing online or printing a 4×6″ print.
You’ll also have the opportunity to purchase larger prints, and all the proceeds go to Arts For Life’s art lessons for pediatric patients!


Registration NOW OPEN!
Capacity limited to the first 1,000 registrants.

We invite you to bring art, music , and poetry lessons to patients and families at Brenner Children’s Hospital by creating a Roll & Stroll fundraising page!

Here are all the amazing reasons why you ought to do it:

  • Is there a better feeling than helping put a smile on the faces of kids and teens who need it the most??
  • Amazing prizes for the top SOLO (individual) fundraiser and for the top TEAM fundraiser. For example: the top TEAM fundraiser will win an awesome prize package from Roll & Stroll sponsor Mast General Store, valued at over $1,000! All generously donated by Mast General Store, so you can rest assured your funds raised will go right to supporting children and teens in the hospital.
  • Depending on how much you raise, you earn some pretty great Roll & Stroll prizes – like t-shirts, sweatshirt hoodies, fleece, and more. You can rock your Roll & Stroll pride all winter long! More details soon.

New This Year: Early Packet Pick-Up!

On Wednesday, November 16, you’ll be able to pick up your registration packet in advance, so you won’t have to wait in line to check in at the event. Your packet will include your wristband, event program, and other important details, plus lots of great swag. BONUS: if you are an early packet picker-upper, you’ll earn a free raffle ticket for a chance to win our Huge Raffle Prize!

  • 11am-1pm at Mast General Store in downtown Winston-Salem
  • 2pm-6pm at Clemmons Bicycle Co. in Clemmons


How long is the route?

New this year: just under 2 miles of twinkling holiday lights!

Where do I park?

This year, we’re starting and ending at the Pool Parking Lot. To park, go in the main entrance of Tanglewood Park (Hwy. 158) and head straight for the guardhouse. Keep going straight (while oohing and aahing over the lights as you drive through) and you’ll be directed to one of three convenient parking lots.

When do I need to arrive?

You must be in the park by 6pm!! Check-in opens and the festivities start at 5pm, and we’ll announce all our big winners for the night at 6:15pm! This includes: prizes for top fundraisers (solo and team), most festive outfit, most decked-out bicycle, and amazing door prizes you’re eligible for just by being there. We suggest getting there early to enjoy the Roll & Stroll Celebration in the Pool Parking Lot – tons of entertainment and fun this year, including:

  • food trucks for dinner (a percentage of proceeds will be donated back to Arts For Life; bring extra money to take advantage of these yummy vendors)
  • free refreshments, courtesy of Krispy Kreme
  • marshmallow roasting station, thanks to Food Lion
  • live performance from Spring Theatre
  • a hands-on art activity, sponsored by Speedball Art
  • visit with Santa and Mrs. Claus (free professional photos of you and your loved ones, for you to download after the event)
  • and more!

If you’re riding a bike, you’ll get the route to yourself from 6:30-7pm. We’ll have a ride leader for you to follow as you take a few spins around the route before putting on the brakes by 7pm to make room for walkers.

If you’re walking, pushing a stroller, pulling a wagon, or accompanying kids on bikes, you’ll enjoy the route starting at 7pm.

You must be in the park by 6:00pm! This will give you and yours plenty of time to park and get settled for the kickoff show, fun and games, food and drink, visits with Santa, and more. Allow MORE time if you haven’t preregistered – but we anticipate a sellout crowd this year, so preregistration’s a great idea! (All Roll & Strollers need to begin walking by 7:30pm). The celebration in the Pool Parking Lot closes at 7:00; the course closes at 9pm.

What do I wear?

Your most festive holiday wear! PRIZES go to the Most Festively Dressed person and the Best Decked-out Bicycle. And, bundle up – layers are your friend! If you have a wagon, pile it up with blankets – better to be warm than sorry.

What if it rains or snows?

We are totally sure that the weather will be delightful on November 17! but this is a RAIN or SHINE event, with no alternate date. In the case of extreme weather conditions, check back here for cancellation notice.

What do I need to bring?

Besides yourself, your friends, your kids, your friends’ kids and your kids’ friends?

  • Flashlights will come in handy
  • Anything twinkly or festive
  • Money for the food trucks, or BYOS(nacks)
  • Warm layers, gloves, hats – we covered all that already, but it bears repeating!

What else is new?

We’ve got a shorter, safer, and overall better route for you this year!

  • No other events or cars will be in the park except Roll & Strollers
  • Plenty of paved parking spots (plus, a limited number of VIP parking spots for sale!)
  • It’s on a Thursday night this year! Mark your calendar: Thursday, November 17.
  • No extra rest stop this year, due to the shorter route – that means Santa and Mrs. Claus and refreshments will all be part of the Roll & Stroll Celebration that starts at 5pm
  • Medic on hand if you need medical assistance
  • Bikers: we’ll have a designated Ride Leader for you to follow, to make it a more community-oriented “group ride,” and learn more about other opportunities throughout the year to ride socially in the Triad.  Feel free to go at your own pace – but follows the rules of the road!

How else can I help???

  • We’re so glad you asked! We need more than 80 volunteers to make sure this event goes off without a hitch.
  • Perks of volunteering include:
    • Lots of great food, drinks, and snacks
    • Snazzy swag and a volunteer lounge area just for you
    • A chance to enjoy the Festival of Lights yourself!
    • Optional: lots of hugs and high fives
  • Click here to choose and sign up for your volunteer spot TODAY. Grab some friends or your officemates and sign up to be on the same team, to make it a bonding, do-good holiday experience.

Huge Raffle Prize:

You can buy tickets for $20 each at the Roll & Stroll, AND if you decide to pick up your packet early on Wed., November 16 (see above), you’ll earn 1 free raffle ticket.

What’s in the Huge raffle Prize Package??  Gift certificates, tickets, and goodies from:

Sawtooth School for Visual Art

Camino Bakery

Wake Forest Athletics

Winston-Salem Dash

a/perture Cinema

Ciccione’s Restaurant

Texas Pete

The Coffee Mill

Hanover Park Winery

Enchanted Cottage

Tanglewood Pizza Company

2520 Tavern

Alex’s Grill & Ice Cream

UNC School of the Arts For Life

Reynolda House Museum of American Art


The Children’s Museum of Winston-Salem

Summit School

The Theatre Alliance

Soccer Unlimited


Styled Gatherings

Shallowford Animal Hospital

And more!


Route Map: