Sip and Stride 5K logo
running

Sip and Stride 5K

Date
September 19, 2026
Distance
Sip and Stride 5K

From the Organizer

Join us for the Sip & Stride 5K, a scenic run (or walk!) through the beautiful vineyard at Running Hare Vineyard, in support of a great cause. This unique event offers a memorable experience for runners and walkers of all levels, combining fitness, community, and a well-earned glass of wine at the finish line. 

All proceeds from the event benefit Holly's Heart Foundation, a 501(c)(3) that partners with various organizations and hospitals to provide families with a memorial keepsake of their loved one's heartbeat recorded inside a legacy bear. For more information please visit our website at: HollysHeartFoundation.org

 

REGISTRATION INCLUDES:

  • Chip-timed 5K run/walk through scenic vineyard, starting at 9 AM. (1 hour time limit kindly requested)
  • Custom Shirt - Adult Unisex or Youth T-shirts. Please register by August 31, 2026 to select your t-shirt size. T-shirts will not be included for registrations after this date.
  • Drink ticket for a complimentary glass of Running Hare Wine (21+ with valid ID)
    • Option to purchase additional, discounted drink tickets during registration.
  • Souvenir Finisher Medal
    • Award pins for Overall Male, Overall Female, and the top 3 Males and Females in the following age groups: 12 & under, 13-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+. 

EVENT DETAILS:

  • Date: September 19, 2026
  • Location: Running Hare Vineyard (Prince Frederick, MD)
  • Start Time: 9 AM
  • Packet Pickup: on Race Day @ 7:30 - 8:30 AM at "Holly's Heart Foundation" tent.
  • Runners and spectators arrive no later than 8:30 AM as portion of course is on the driveway and it will be closed at 8:45 AM.
  • Race is rain or shine. No transfers or refunds.
  • No strollers or dogs allowed on course.
  • Spectators welcome. Winery open for business during and after race.
  • Walkers and children are welcome to participate. Registration is required and will start on time at 9 AM behind the runners for safety of all participants.

Distances & Pricing

Sip and Stride 5K9 AMRegister →

Race Location

About This Sport

From Endurance Grid's Founder

Endurance Grid is here to help you understand the sport, decide if it's the right fit, and learn how to prepare. For course distances, logistics, and race-day specifics, always defer to the race organizer's event page.

With running, there's a distance for every fitness level, a community at every start line, and nothing beats the feeling of crossing a finish line you trained for.

Running is an endurance sport that rewards consistency, and showing up every week compounds in ways that will surprise you.

Running

From 5K to marathon, running races are the most accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.

Frequently Asked Questions (FAQs)

What is the Sip and Stride 5K?
Sip and Stride 5K is a running event held in Prince Frederick, MD. Learn more about the different endurance sports here.
When and where is the Sip and Stride 5K?
Saturday, September 19, 2026 in Prince Frederick, MD at Running Hare Vineyards, Prince Frederick, MD. Check the official event page for exact start times and wave schedules.
How do I register for the Sip and Stride 5K?
Registration is handled through their official registration page. Confirm pricing, distances available, and sign up there.

Sip and Stride 5K

Sep 19, 2026

Register →