Day Trips
Surebridge Mountain 8.5-Mile Hike

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A Rugged 8.5 Miles on the Appalachian Trail and Long Path

Great new hike on some famous trails: the AT and the Long Path. We will hike past four notable geologic features while taking in the views of the Hudson Highlands.

Join other outdoor enthusiasts as we follow a series of winding trails in an area known for its numerous lakes and impressive views. There is magnificent scenery along the way and lots of climbing over this highly metamorphosed ridge system. Our loop route will take us to a lake halfway and over many twisting trails both ways.

Event Intensity Level

At a total of eight miles, this hike is considered moderate to challenging and is Intensity Level 3-4. Read a full description of all levels.

lake skenonto hike

Event Details

  • Bring Lunch and 3L of water minimum, per person; weather-appropriate clothing. We are not kidding about the 3L of water!
  • Departure 9:00 AM (Arrive at 8:45 for check-in.)
  • Return Approximately 6:00 PM
  • Departure and Return Location Northeast corner of 73rd Street and Broadway (In front of Apple Bank). Subways 1, 2, 3 to 72nd Street.

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Intensity Levels

This event or trip is Intensity Level 3 - 4.

Overview > Adventures at All Skill Levels

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We offer adventures for everyone, no matter what your skill level. This guide will help you decide which trip is right for you.

  1. Activity

    How long (in hours) you may be active every day during the trip.

  2. Distances

    You should feel confident that you would be able to complete these distances every day of your trip.

  3. Surfaces

    What types of terrain you may encounter and should be prepared for on your trip.

  4. Elevation Change

    The largest elevation change you may encounter on your trip.

  5. Altitude

    The highest elevation you may reach on your trip.

Level 1 > Laid-Back, Unhurried, Restful

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  1. Activity

    1 – 3 hours

  2. Distances

    Walk or hike less than 3 miles

  3. Surfaces

    Flat terrain

  4. Elevation Change

    Little or none

  5. Altitude

    Less than 3,000 feet

Level 2 > Easy Active — Perfect for Active First-Timers

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  1. Activity

    2 – 5 hours

  2. Distances

    Hike up to 6 miles, cycle 10 – 30 miles most days

  3. Surfaces

    Flat or rolling terrain with some steeps possible

  4. Elevation Change

    Up to 1,500 feet per day

  5. Altitude

    Up to 6,000 feet

Level 3 > Moderate — for Novices & Above

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  1. Activity

    4 – 6 hours most days

  2. Distances

    Hike up to 10 miles, cycle 20 – 40 miles most days

  3. Surfaces

    Rolling or mountainous terrain with some steeps

  4. Elevation Change

    Up to 2,000 feet per day

  5. Altitude

    Up to 10,000 feet

Level 4 > Vigorous — Recommended for Fit Travelers with Basic Skills

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Experience required.

  1. Activity

    5 – 8 hours most days

  2. Distances

    Hike up to 12 miles, cycle 30 – 50 miles most days

  3. Surfaces

    Mountainous, exposed terrain with steep ascents/descents and uneven trails

  4. Elevation Change

    3,000 feet per day

  5. Altitude

    Up to 14,000 feet

Level 5 > Strenuous — Very Fit or Experienced Travelers

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Experience required; doctor’s release may be required (if so, will be noted in trip description).

  1. Activity

    10 plus hours per day

  2. Distances

    Hike 12 or more miles, cycle 50 miles most days

  3. Surfaces

    Remote mountainous, exposed terrain with steep ascent and descents, uneven trails with loose features

  4. Elevation Change

    Up to 4,000+ feet per day

  5. Altitude

    May well exceed 14,000 feet

Outdoor Bound Hang Gliding Adventure

Hang Gliding Adventure

Experienced, Fun & Qualified Guides

From cycling across the United States to leading horse treks through New Zealand to scaling Nepalese peaks, Outdoor Bound guides have real-world outdoor experience. Collectively, they have hiked, biked, climbed and kayaked tens of thousands of miles around the globe.

Whether their professional backgrounds are as teachers, personal trainers, artists, environmentalists or business leaders, they all have an extensive knowledge of the natural world and local history. Each guide has also passed a rigorous guide certification program and is trained in wilderness first aid or as a Wilderness First Responder.

Diverse & Interesting Groups

There is no typical Outdoor Bound participant. While ages typically range from 20 to 50, those who come to experience outdoor adventure range from singles to couples, from lawyers to waiters. They are a mix of women and men. While the group is always diverse, you will certainly feel welcome. Our guides go the extra mile to make the atmosphere of each trip social and fun. Many people in the Outdoor Bound community have forged lasting friendships as a result of our trips.

New Experiences

Skydiving, ice-climbing, hot-air ballooning, skiing and hiking every weekend are just a few of Outdoor Bound’s year-round adventures. These trips are accessible to everyone, including the novice, who might feel a little uneasy, the young urban professional trying to get away and even the adrenaline junkie looking for a new rush.

Environmental Awareness

“Leave nothing but footprints, take nothing but pictures,” is the Leave No Trace motto embraced by Outdoor Bound. From purchasing bamboo T-shirts to printing with soy-based inks on recycled paper, Outdoor Bound strives to create the least environmental impact possible while on trips and in the office.

Outdoor Bound Singles Hike Fourteen Peaks

Singles Hike Fourteen Peaks

Other Trips in This Category

  1. 3rd of July Hike & Swim
  2. 4th of July Hike & Swim
  3. Autumn Glider Soaring
  4. Autumn Mohonk Scramble Challenge
  5. Awosting Falls
  6. Backcountry Snowshoe on Russian Bear Mountain
  7. Backwoods Snow Sledding
  8. Backwoods Snowshoeing
  9. Backwoods Snowshoeing: Catskill Mountains, High Point
  10. Backwoods Snowshoeing: Catskills, Panther Mountain
  11. Backwoods Snowshoeing: Catskills, Slide Mountain
  12. Backwoods Snowshoeing: Surebridge Mountain
  13. Black Ash Mountain Hike
  14. Black Rock Hike
  15. Breakneck Ridge Hike & Scramble
  16. Breakneck Ridge Hike to Mount Taurus
  17. Bullets, Beer & BBQ
  18. Canoe & Kayak
  19. Canoeing, Camping & Hiking in the Adirondacks
  20. Canopus Lake Hike
  21. Castle Ruin Hike
  22. Catskills Hike & Rappel: Panther Mountain
  23. Catskills Hike: Indian Head Mountain
  24. Catskills Hike: Panther Mountain
  25. Catskills Hike: Slide Mountain
  26. Catskills Hike: Sugarloaf Mountain
  27. Catskills Snowshoeing & Rappelling
  28. Class V Whitewater Rafting
  29. Clay’s Private Rock Climbing, Hiking & Camping Weekend
  30. Columbus Day 6 Mile Hike: Gertrude’s Nose in Minnewaska
  31. Cross Country Ski & Snowshoe
  32. Diamond Mountain Hike
  33. Dog, Beach & Vine
  34. Echo Lake Hike
  35. Empire Hotel Rooftop Cocktails & Gear Raffle
  36. Evening Horseback, Hayride & Cookout
  37. Fall Foliage Hike, Apple & Pumpkin Picking
  38. Flamenco Lesson, Dinner, Drinks & Performance
  39. Fourteen Peaks Hike
  40. Fourth of July Skydiving!
  41. Full Moon Halloween Hike
  42. Full Moon Hike
  43. Full Moon Kayaking to Abandoned Castle
  44. Gertrude’s Nose 6 Mile Hike in Minnewaska
  45. Groundhog Day Hike: Russian Bear
  46. Gunks Hike & Whiskey Tasting
  47. Gunks Horseback Riding & Whiskey Tasting
  48. Gunks Winter Hike & Whiskey Tasting
  49. Half Day Hudson Valley Biking, Hiking & Pub
  50. Halloween Hangover Hike: Ramapo Ridge 9 Miles
  51. Halloween Horseback Riding & Wine Tasting
  52. Hang Gliding Adventure
  53. High Peterskill Hike in Minnewaska
  54. High Ridge Hike & Yoga
  55. High Ropes Climbing
  56. Hike & Art Gallery
  57. Hike & Hound 6-Mile Hike
  58. Hike & Hound Eight Mile Hike
  59. Hike & Pilates
  60. Hike & Wine Tasting
  61. Hike The Great Escape
  62. Hike the Hamptons
  63. Hike, Swim, Wine Tasting & Grateful Dead Tribute
  64. Hike, Swim, Wine Tasting & Harvest Moon Folk Festival
  65. Hike, Swim, Wine Tasting & Johnny Cash Tribute
  66. Hike, Wine & Charcuterie Tasting
  67. Hike, Wine & Fondue Dinner: Appalachian Trail
  68. Hike, Wine & Fondue Dinner: Ship Rock Ridge
  69. Hike, Wine & Fondue Dinner: Tom Jones Mountain
  70. Hike, Wine & Fondue Tasting: Tom Jones Mountain
  71. Hike, Wine & Shakespeare in the Orchard
  72. Hike, Yoga & Swim
  73. Holiday Ice Skating at Bryant Park
  74. Holiday Ice Skating at Bryant Park
  75. Holiday Party at Country Club
  76. Hollywood Stunt Class: High Falls
  77. Hollywood Stunt Class: Trampoline
  78. Horseback & Art Gallery
  79. Horseback & Hike
  80. Horseback Riding & Wine Tasting
  81. Horseback Riding and Introduction to Polo
  82. Horseback, Wine Tasting & Apple Picking
  83. Hot Air Ballooning
  84. Hudson Half Day Sailing & Hike
  85. Hudson River Brunch Sailing Excursion
  86. Hudson Sailing & Hike
  87. Ice Climbing
  88. Indoor Rock & Pints
  89. Indoor Rock Climbing
  90. Intro to Dragon Boat Racing
  91. Iron Mine & Lemon Squeezer Hike
  92. Kaaterskill Falls Eight Mile Hike
  93. Kristin’s Private Hike, Wine & Fondue Tasting
  94. Labor Day Hike: High Peterskill in Minnewaska
  95. Labor Day HIke: Lake Skenonto
  96. Lake Skenonto Hike
  97. Lake Skenonto Hike & Swim
  98. Leave No Trace Educational Hike
  99. Leave No Trace Two-Day Trainer Course
  100. Memorial Day Fourteen Peaks Hike

Bringing a Friend or Two?

Please be sure to enter the total number of people in the Qty box. In addition, be sure to include your friends’ names and cell-phone numbers on the final Checkout page. The final discount price is the price per person, multiplied by the Qty you enter.

Reminder about Winter Trip Conditions

We closely monitor snow, ice and related weather conditions before each trip. Lack of snow or similar, unsatisfactory weather/trail/river conditions may lead to changes to the trip or rescheduling or cancellation.

Please consult the individual trip description or Event Calendar for notice of any such changes. Refer to our full Policies page for more information about reservations and cancellations.

Register > Surebridge Mountain 8.5-Mile Hike

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