Stissing Triathlon
Pine Plains, United States · June · Independent (Wilson Endurance Sports)
Why people love it
- No cutoff times, and the last finisher is cheered in
- Lifeguards and kayakers on the swim, with rests allowed beside a kayak or buoy
- Hybrid and mountain bikes allowed, but no e-bikes
- Parking close to transition, with packet pickup Saturday or on race morning
- Beach picnic after the race, and athletes call the setting beautiful
Watch out for
- Bike is hilly over 20.3 km (12.6 mi), with a named climb on Sigler Hill Road
- Swim was cut to about 457 m (500 yd) in 2025 after lightning
- Roads were slick in 2025 and gravelly at one turn in 2023
- Small field of about 100, so the course can feel spread out
- Albany airport is about 105 km (65 mi) away, so plan to drive
Race
How racers feel about it, how well it is run, and how it treats a first timer. Counts for 30% of the overall score.
Toughness: Tough
- Racer satisfactionLoved4.2
Three local reports from 2023 to 2026 are positive, and 2025 athletes called it one of the most beautiful local races. · Medium confidence
- OrganizationWell run4.1
Same directors for eight years, fire and police support, and a quick weather decision in 2025. Everyone finished both years reported. · Medium confidence
- First timer friendlyFriendly4.2
No cutoffs, kayakers and any bike allowed, but the bike is hilly. · Medium confidence
Course traits, not part of the score
- PR potentialAverage3.0
Hilly bike, though 67 athletes set personal bests in 2023. · Low confidence
Swim
Wetsuit odds, water temperature, calm, and the experience of the start. Counts for 16% of the overall score.
- Wetsuit legalUsually3.5
Late-June lake temperature is not published. 2026 water felt a bit warm, and the USA Triathlon limit is 25.6 °C (78 °F). · Low confidence
- Water temperatureComfortable3.6
Cool in the 2025 drizzle, a bit warm in 2026. No temperatures published. · Low confidence
- Calm waterMostly calm3.5
Small lake. Lightning and chop shortened the 2025 swim, but 2026 had no wind. · Medium confidence
- Swim easeEasy4.0
730 m (800 yd) in a small lake with kayakers. · Low confidence
- Swim experienceGreat3.9
Athletes called the setting beautiful in 2025. Water clarity is not described. · Low confidence
- Swim supportGood4.4
Certified lifeguards and volunteer kayakers, with a rest beside a kayak or a personal buoy allowed. · Medium confidence
Bike
Road surface, closures, scenery and wind. Counts for 18% of the overall score.
- Road surfaceGood3.6
The 2026 winner called the roads smooth. A rider skidded on a gravelly turn in 2023. · Low confidence
- Road closuresPartly closed3.2
Police and fire help on course. Whether roads are closed is not published. · Low confidence
- Bike sceneryBeautiful4.2
Hudson Valley countryside under Stissing Mountain. Athletes praised the beauty in 2025. · Low confidence
- WindMostly calm3.8
The 2026 race director reported no wind. Other years are not described. · Low confidence
Course traits, not part of the score
- Bike speedAverage2.9
Hilly with Sigler Hill Road. Wet roads in 2025 and a gravelly turn in 2023. · Medium confidence
- Bike flatnessRolling2.8
Described as hilly. Gain is not published. · Low confidence
- Bike simplicitySome technical parts3.2
Hilly rural roads with some turns where gravel collects. · Low confidence
Run
Crowds, aid stations, conditions underfoot and scenery. Counts for 13% of the overall score.
- Crowd supportDecent3.0
Field of about 100 and mostly local volunteers. · Low confidence
- Aid stationsGood3.6
The aid station and finish stay open for walkers. Little else is described. · Low confidence
- Run sceneryBeautiful4.1
Lake loop below Stissing Mountain. · Low confidence
- Run conditionsEasy3.8
Short 5.3 km (3.3 mi) run with an 8:00 am start. · Low confidence
Course traits, not part of the score
- Run flatnessRolling3.4
Loop around the lake. Elevation gain is not published. · Low confidence
Conditions
Air temperature, how predictable the weather is, setting, and spectating. Counts for 13% of the overall score.
- Air temperaturePleasant4.1
Late June ranged from 18 °C (65 °F) in 2025 to 24 to 26 °C (75 to 78 °F) in 2026. · Medium confidence
- Weather reliabilityVariable3.0
Lightning in 2025 shortened the swim and nearly turned the race into a duathlon. · Medium confidence
- Venue beautyLovely4.3
Lake below Stissing Mountain, and 2025 athletes called it one of the most beautiful local races. · Medium confidence
- Spectator friendlyEasy3.8
Lake and beach site with transition and finish close together. · Low confidence
Course traits, not part of the score
- Low altitudeSea level4.6
About 160 m (525 ft). · Medium confidence
Stay and travel
Hotels, walkability, getting there, and the town around the race. Counts for 10% of the overall score.
- Hotel availabilityBook early3.2
Small town, so lodging is in nearby villages. · Low confidence
- Hotel valueNormal3.2
Hudson Valley weekends can be pricey. · Low confidence
- WalkabilityWalkable4.4
Parking is very close to transition at the race site. · Medium confidence
- Travel easeOne connection2.8
Albany airport is about 105 km (65 mi) away, so most athletes drive. · Low confidence
- LogisticsSimple4.3
Single site, packet pickup Saturday or from 5:30 to 7:40 am on race day, and an 8:00 am start. · Medium confidence
- Town and foodFine3.2
Small village. A beach picnic with simple treats follows the race. · Low confidence
Key facts
- Location
- Pine Plains, NY, United States
- Typical month
- June
- Latest or next date
- 27 June 2027
- Organiser
- Independent (Wilson Endurance Sports)
- Field size
- About 100 athletes
- First held
- 2019
- Distances
- 0.8 km (0.5 mi) swim, 20 km (12.4 mi) bike, 5 km (3.1 mi) run
- Swim venue
- Stissing Lake (Stissing Pond), Pine Plains (lake)
- Wetsuit
- Optional (recommended)
- Key climbs
- Sigler Hill Road
- Air temperature
- 18–26 °C (64–79 °F)
- Altitude
- 160 m (525 ft)
- Nearest airport
- Albany (ALB), 105 km (65 mi) away
- Booking
- Small Hudson Valley town; lodging in nearby Millbrook, Rhinebeck, Hudson.
What racers and reviewers say
- New Pine Plains HeraldRaced 2026 · article · Positive
Report on the 8th edition: about 100 athletes from 11 states, everyone finished. Race director described sunny, windless 75 to 78 °F (24 to 26 °C (79 °F)) weather. The winner called it a great race with strong competition and said the lake was a bit warm and the roads smooth.
“a great race”
- New Pine Plains HeraldRaced 2025 · article · Positive
2025 race in drizzle and about 65 °F (18 °C): lightning before the start nearly forced a duathlon, swim cut to about 500 yd (457 m (1,500 ft)), roads slick, hilly bike with Sigler Hill Road. Athletes called it one of the most beautiful local races and a mental and physical challenge. 96 triathletes, all finished; fire and police help.
“one of the most beautiful local races”
- Lakeville JournalRaced 2023 · article · Positive
2023 results report: about 100 athletes, sunny after a wet week, 67 personal bests posted and several course records. A regular since 2010 calls it a yearly tradition; one rider skidded on a gravelly bike turn. Beach picnic after.
Raced Stissing Triathlon? Your notes on the course, conditions and logistics help the next athlete decide.
Sources
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