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.
Events
Weather
Typical Conditions
It's too far out for a forecast, so here's what weather on this date is normally like in the area. A race day forecast will replace this as race week approaches.
Typical High
76°
Typical Low
57°
Chance of Rain
27%
Based on US Climate Normals data from Mechanicsville 5 Ne, 8 mi from the venue.
Host City
About Prince Frederick, MD
Elevation
161 ft
Nearest Airport
DCA
Ronald Reagan Washington National Airport · 32 mi
Time Zone
Eastern Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
Your Next Start Line
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Sip and Stride 5K, put it on the calendar, and turn “someday” into a start date.
103
Days to train
- Race
- Sip and Stride 5K
- Date
- September 19, 2026
Coming Up
More Running races near Prince Frederick, MD
Corteau Vineyards Wine Run 5k
5K
10 miles away
Run to the Taproom - Mully's Brewery Father's Day 5K
5K
Less than a mile away
Neon Nights 5K
5K
7 miles away
Totally Awesome 80's Run
Less than a mile away
From Endurance Grid
About This Sport
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 race held in Prince Frederick, Maryland on September 19, 2026. It is one of the many endurance events listed on Endurance Grid, a multi-sport endurance event calendar covering running races, triathlons, HYROX, and more endurance sports across the United States. Find more running races near you or explore our sports guides to learn what race day actually feels like.
- When and where is the Sip and Stride 5K?
- Saturday, September 19, 2026 in Prince Frederick, Maryland at Running Hare Vineyards, Prince Frederick, MD. Check the event page for exact start times and wave schedules.
- How do I register for the Sip and Stride 5K?
- Registration is handled through the event's registration page. Confirm pricing and distances there, and sign up.
Sip and Stride 5K
Sep 19, 2026