2026 Point to Point Challenge of the Year Submissions Open June 1, 2026
Submissions are OPEN June 1st to October 31st, 2026.
Event Description: Complete and submit a Point to Point Challenge from June 1st to October 31st to be entered into the event. Point to Point Challenges include a run, swim, bicycle, paddle, or climb of a POINT to POINT line (route) in the natural geography.
EX: Swim or paddle across a body of water, bike across a land mass, climb a mountain ect.
Whether it be bicycling, swimming, paddling, running or hiking a Dawgpatch Point to Point Challenge involves getting from location ‘A’ to location ‘B’ (Point to Point) by self-powered means. Unlike traditional events that adapt a predetermined physical activity into an area or course, we allow the natural geography of a specific area to produce new and innovative challenges. In order to achieve this we follow a “SEE, MAP, EXECUTE” approach.
First: Observe and reflect on the area around you = SEE.
Second: Map potential challenges, plot routes, and determine proper modes of travel/traverse = MAP.
Third: Complete the challenge effectively and safely = Execute.
Some recommended distances can be referenced in our 100 Point Challenge BUT these distances are NOT absolute for this event. Get creative and push your own physical and mental limits, and let the people decide who puts up the best Point to Point Challenge of the Year. Voting will take place in November, after the event end date (October 31st) by previous Dawgpatch Challengers. Voting will be based on the following criteria.
Point to Point Challenge Voting Considerations:
Geographical significance of the POINT TO POINT chosen
Mode of travel within geography chosen (Run, Swim, Bicycle, Paddle, Climb or combination of multiple)
Distance
Route choice and route finding (exposure, difficulty, directness)
Nature of completion (Levels of Support?) Was this Point to Point completed solo and unsupported? Was there a support boat or van trailing? Were you carrying all of your gear or did you have resources dropped off along the way?
Overall design and execution
Get out and get after it this season. All challenges submitted will be posted on the Dawgpatch Bandits instagram and website challenge page to keep people up to date on POINT TO POINT Challenges being thrown down. *NOTE you can submit more than one challenge per season. Please reference previous challenges completed to get ideas, get inspired, and get clarity on what a Dawgpatch Point to Point Challenge looks like when deciding your own challenge to attempt.
IMPORTANT:
*You must FILL OUT and SUBMIT the Point to Point Challenge form below with the required information to be entered into the event.
Start Point & End Point
Mode of Travel (EX: Run, Swim, Bike, Paddle, Hike)
Distance
Date of Completion
Levels of Support
Map (with route)
At least one image and/or video from the completed P2P challenge.
Trip Report / Additional Details (Can be brief)
All individuals who submit a Point to Point Challenge in 2026 will receive a Skull’n Dagger Patch and shop item of their choosing.
The Point to Point Challenge of the Year winner will receive a custom Skull’n Dagger challenge jersey with the winning Point to Point featured on the back.
IF you want to make your Point to Point Challenge a fundraiser for Dawgpatch Bandits Inc. please follow this link: Make Your Point to Point Challenge a Fundraiser.
GET AFTER IT!
POINT TO POINT CHALLENGE FORM
2026 CHALLENGES: OPEN
CHECK OUT SUBMISSIONS FROM PREVIOUS YEARS TO GET INSPIRED
2025 CHALLENGES: CLOSED
2025 WINNER: LIGHT TO LIGHT RUN : (Fire Island to Montauk Pt.)
FULL COLLECTION: 2025 P2P CHALLENGES SUBMITTED
2022 CHALLENGES
*2022 WINNER: GRAND CANYON RIM2RIM2RIM*
FULL COLLECTION: 2022 P2P CHALLENGES SUBMITTED
2021 CHALLENGES
Stand Outs:
*PLUMB ISLAND PUNCH: SWIM*
&
*RIDE FOR RECOVERY: NORTHERN U.S. BIKEPACK*
FULL COLLECTION: 2021 P2P CHALLENGES SUBMITTED
Orient Pt. to Montauk Pt. Bike 🏴☠️ (2021)
Jessups Neck to Southold Swim 🏴☠️ (2021)
Plumb Island Punch: Swim 🏴☠️ (2021)
2021 Ride for Recovery: Northern Bike Across the U.S 🏴☠️ (2021)
2020 CHALLENGES
*2020 STANDOUT: GREAT PECONIC BAY SWIM*
FULL COLLECTION: 2020 P2P CHALLENGES SUBMITTED
Noyac Bay Swim 2020 🏴☠️ (2020)
Little Peconic Bay Swim 🏴☠️ (2020)
Great Peconic Bay Swim 🏴☠️ (2020)
Orient Point to Montauk Point Paddle: SUP 🏴☠️ (2020)
Barcelona Connection: Swim 🏴☠️ (2020)
2019 CHALLENGES
STANDOUTS:
*GARDINERS BLITZ SWIM*
&
*BRITISH ISLES BIKE TOUR*
FULL COLLECTION: 2019 P2P CHALLENGES SUBMITTED
Shinnecock Shoreline Challenge 🏴☠️ (2019)
Maine: Patch Paddle 🏴☠️ (2019)
Vashon Island Challenge: Swim Run 🏴☠️ (2019)
Gardiners Blitz Swim 🏴☠️ (2019)
Ponquogue to Sea Tuck Cove: SUP 🏴☠️ (2019)
Cedar Point 4: Swim 🏴☠️ (2019)
Montauk Marathon: Run 🏴☠️ (2019)
British Isles Conquest: England, Scotland, Ireland Bike 🏴☠️ (2019)
2018 CHALLENGES
THE ORIGINAL
*RAISING AWARENESS: CROSS COUNTRY BIKE TOUR*
FULL COLLECTION: 2018 P2P CHALLENGES SUBMITTED
Twin Forks Run, Swim, Run, Swim, Run 🏴☠️ (2018)
Shelter Island Swim 🏴☠️ (2018)
Isle Chora Open Ocean Swim 🏴☠️ (2018)
2018 Raising Awareness Cross Country Bicycle Tour 🏴☠️ (2018)

