The Sip and Stride 5K starts at 9:00 AM, giving you a reasonable window for arrival and pre-race preparation on race morning. Held at Running Hare Vineyards in Prince Frederick, Maryland, this event offers a 1-mile running distance. Entry fees range from $44 to $48, making it an affordable option for a local race day. The September timing means moderate early fall conditions in Maryland. If you're traveling to the area for the race, plan to arrive with enough time to check in, warm up, and familiarize yourself with the vineyard venue layout before the starting gun.
From the Race 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.
Hotels Near This Race
Find accommodation close to the start line in Prince Frederick, MD. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
Race Travel Insurance
Don't forget travel insurance for September 19.
You've trained for months and booked a trip to Prince Frederick, MD.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Sip and Stride 5K 2026 — Prince Frederick, MD?
Sip and Stride 5K 2026 — Prince Frederick, MD takes place on September 19, 2026. The race is held in Prince Frederick, Maryland.
Where is Sip and Stride 5K 2026 — Prince Frederick, MD held?
Sip and Stride 5K 2026 — Prince Frederick, MD is held at Running Hare Vineyards in Prince Frederick, Maryland.
Where can I find hotels near Sip and Stride 5K 2026 — Prince Frederick, MD?
RaceHotelFinder shows hotels sorted by distance from the race venue in Prince Frederick. Use the map or list view on this page to compare options and book race weekend accommodation.
