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To those in our NY/NJ/PA/CT hiking and outdoor community, the PROACTIVE Challenge is back and we've made some additions to make it more fun, more competitive, and more interesting than the inaugural edition! If you enjoy spending your time scrambling up Breakneck Ridge, casually walking long distances through Harriman, or moving for miles in some fashion, this competition is for you!

The PROACTIVE champion is decided in a year-long, points-based competition built around a series of challenges, both group and solo, that will require and test strategic planning, prioritization, and dedication. It's designed for any hiker - novice to veteran - as anybody could potentially win by piecing together the best overall year. 

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This is the second PROACTIVE Challenge and the original proved that anything can happen. People will all tackle this competition in their own way - the winner may be a new hiker who wanted new places to go and decided to check off our list or the winner could be an accomplished ultrarunner who eats these challenges up and spits them all out. It's a casual competition that will slowly truck along in the background over 12 months as participants tend to their own busy lives and needs.

The goals of the PROACTIVE Challenge are...

  • To promote a proactive lifestyle; to inspire and motivate people not to take time for granted, to satisfy their appetite for adventure, to improve their overall level of wellness, to expand their social circle, to push their own limits, and to thrive now.

  • To showcase the beauty and diversity of our region.

  • To help novice hikers discover new places to hike and encourage them to continue advancing.

  • To provide advanced hikers with supplemental prep or training for larger events and general exercise.

  • To bring our hiking/outdoor community together and build new social connections and networks.

  • To highlight and support worthwhile causes of interest to our community at large and to our participants.

  • To have a fun time doing all of this...



Each event can only be completed once within the designated time period. Multiple completions for the same challenge will not earn additional points.

* Will be held as social event. Attendees earn 5+ Points.

Each challenge must be satisfied by an individual hike.

By May 31, 2025

Devil's Path in a Day

Complete the Devil's Path in a Day -  50 Points

Hike 30+ Miles in the Palisades - 40 Points

By May 31, 2025

Easy Anywhere
Sunrise Bonus
Harriman Moderate
Breakneck 7

Sun Pop: Year II - 10/15/20/25/30/35 Points *

Hike 7+ Miles in New York - 15 Points

Hike 5+ Miles in New Jersey - 10 Points 

Bonus - Hike 1.5+ Miles to a Sunrise - 10 Points


BBQ Bonus

Complete Schunemunk Tour - 30 Points & Patch *

Hike 1500' of Elevation - 15 Points

Bonus - Attend PROACTIVE Barbeque - 10 Points


Easy Hudson River Hike
Complete a 7+ mile hike.
Easy Hudson River Hike

Hudson Highlands Tour - 30 Points *

Hike 7+ Miles in the Catskills (or North) - 15 Points

Hike 1500' of Elevation - 10 Points

Hike 3+ Miles to Any Fire Tower - 10 Points 

Bonus - Hike 5+ Miles to Foliage  - 10 Points


Easy Hike In New York
Bonus Creepy Hike
Hudson Highlands State Park Hike


Easy Hike
Catskills or Adirondacks Hike
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Hike 20+ Miles Anywhere - 35 Points

Hike 7+ Miles Anywhere - 15 Points

Hike 5+ Miles to Any Ruins - 10 Points

Bonus - Attend a PROACTIVE Creepy Hike - 10 Points *

 Complete Winaki Derby or NGT - 30/35 Points & Patch *

Hike 5+ Miles to a View of the DWG or Hudson - 10 Points *

Hike 10+ Miles OR 2000 Feet of Elevation - 15 Points



Hike 15+ Miles Anywhere  - 20 Points 

Hike 10+ Miles Anywhere - 15 Points

Hike 5+ Miles Anywhere - 10 Points *

Bonus - Attend The Proactive Dinner - 10 Points


Snow hike
Beacon Bully 2024

Complete Beacon Bully - 30 Points & Patch *

Hike 2500' of Elevation - 15 Points

Hike 7+ Miles Anywhere - 10 Points *

Bonus - Hike 1.5+ Miles Hike In Snow - 10 Points


Hike 18+ Miles Anywhere - 20 Points *

Hike 7+ Miles in Harriman - 10 Points

Hike 10+ Miles and Double Summit - 15 Points

Bonus  - Hike 3+ Miles with Another Person - 10 Points


Hike 22.5+ Miles - 35 Points *

Hike 7+ Miles in the Hudson Highlands - 10 Points

Hike 10+ Miles in NJ - 15 Points *

Bonus - Hike 5+ Miles Anywhere - 10 Points


Easy bonus hike.

Hike Any PROACTIVE Patch Route (Except GOTH) - 35 Points *

Hike 10+ Miles - 10 Points

Hike 3000' of Elevation - 15 Points

Bonus - Hike 5+ Miles and Over Any Bridge - 10 Points


Sunset hike
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Complete GOTH - 30 Points & Patch *

RUN 5+ Miles - 10 Points

Hike in NY (5+ Miles) & NJ (3+ Miles) in One Day - 15 Points

Bonus - Hike 3+ Miles to a Sunset - 10 Points


Hike 10+ Miles in the Catskills.

65 Points

35 Points

Task Points

50 Points - Record a 30-second video about the Challenge.

50 Points (10 per)  - Submit content for a social media story.

20 Points (5 per)  - Submit content for a social media post.

50 Points - TBD


20 Points (10 per)  - Climb any fire tower.

50 Points - TBD

30 Points - TBD

20 Points - TBD

Bonus Points


20 Points -  Achieve ELITE Status

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20 Points -  Earn ALL 4 Patches


70 Points (5 per)  - Attend a Social Hike

100 Points (10 Per) -  Complete all challenges in a month (Aug-May)

20 Points -  Complete ALL Bonus Challenges

30 Points - Halfway Leader


20 Points (10 per)  - Best Efforts

30 Points - TBD




1. Participants must complete at least one challenge per month to remain in the competition after October 1st. All challenges must be completed within time periods indicated to earn points.

2. To be eligible for bonus points, a participant must complete both the bonus activity and at least one other challenge listed for the corresponding month.

3. To earn points for self-tracked challenges, participants must

(a) complete the challenge within its designated time limit, (b) track the challenge on Strava, or a comparable, shareable tracking app, (c) send the track and the pictures to The submitted track must show participants' name, map of track, and elapsed time.

Participants using STRAVA will have their points automatically counted when they share their profile. Other tracking apps must follow the guidelines above.

4. Registration for group events will be scheduled in advance or could be 'pop-ups' that will be announced on @proactiveahw social media (Instagram, Facebook, TikTok) and on our website with sufficient notice. 

5. Participants who attend group events will receive 5 additional points. If a participant does not attend the group event, they can complete the same route at any time during that same month.

6. The leaderboard will be updated bi-weekly and made available on the website.

7. The participant with the most points at the end of the year will be the 2024-2025Proactive-AHW Champion and will receive a cash prize ($1000.00). A 2nd and 3rd place medal and other prizes will be awarded to the 2 subsequent participants based on points.

8. If there is a tie at the end of the season, the tie will be broken through attrition based off of statistics collected from each challenge throughout the year. If a winner is still not apparent based off of the existing statistics, participants involved in the tie will be asked to submit 10 additional personal solo accomplishments completed between June 2024-May 2025 for the consideration of a panel. If a winner is still not apparent based on the existing data, a public vote will be held to determine the winner of which the constituency would be pulled from participants, partners, and followers. Belts, medals, and cash prizes will be awarded in August at the 2025 PROACTIVE BBQ.

9. Particular instructions will be provided for some bonuses, tasks, or challenges (when applicable).

10. Unless a specific location is indicated in the Challenge listing, any distance or elevation challenges may be satisfied anywhere as long as it is outdoors. Indoor walks or runs or anything on a treadmill or other exercise equipment will not earn points.

11. This is meant to be primarily for fun and the competition involved should be primarily the participants competing with themselves. Have fun!


June 30, 2024

2023-2024 Champion


Vanessa Vaglio

756 Points

Vanessa held on to the lead for much of the early portion of the Challenge before others began nipping at her heels. Until, that is, she completed the Devil's Path (and a half!) in the final month of the competition to climb back to #1, finishing up the last few challenges and securing the win! She earned all four PROACTIVE patches, earned Elite status for the second time, ran the Breakneck marathon (and half), completed Breakneck 7.5 and Minnewaska Tour, among other things. Her attention to detail and running prowess helped her edge out the rest and successfully defending the belt and becoming a two-time champion!

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Justin Lewandowski
746 Points

Phil Lombardo
740 Points

726 Points

2022-2023 Champion


Vanessa Vaglio

Inaugural PROACTIVE champion, Vanessa Vaglio, was awarded the championship due to her dedication and progression between June 2022 and June 2023. Vanessa completed a majority of our most difficult hikes, competed in the Breakneck Marathon 2023, and rigorously prepared and trained in the build-up to the aforementioned. Of all participants, she most embodied the spirit of PROACTIVE during the 2022-2023 season. 

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