Day Trips
Hike, Swim, Wine Tasting & Grateful Dead Tribute

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A day of woods, exercise, wine & The Dead!

No rings of fire here; just a rugged six mile hike to a pristine lake, where we will swim and have lunch. Then onto a winery in the Hudson Valley for a wine tasting and live Gratetful Dead tribute!

Burn some calories on an invigorating 6 mile, medium-intensity hike through gorgeous summer trails and wild blueberries, lunching and swimming at the lake. Then on to a wine tasting at a top Hudson Valley winery. After sampling 5 wines (and buying more for the picnic, if you wish) we will spread our blankets and settle in for a picnic dinner, compliments of a CIA-trained chef, as we watch the sun set…then enjoy a live tribute to The Dead by four different live bands.
The PERFECT summer day escape—exercise, live music & indulgence!

Hike

We will work hard on the first 2.5 miles, where we climb up, up, up to a high section of the Hudson Highlands. You need to be in good physical shape for this hike! 6 miles total. On a clear day, you can see 4 states. This handsome trail is notable for some steep and rocky sections that provide spectacular views.

Our beautiful loop trail takes us to a secluded lake, where we’ll swim&lunch (bring your own) and relax. There is a wide variety of fascinating vegetation and terrain along our path.

This hike is Intensity Level 3. Read a full description of all levels.

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Winery & Performance

Our winery is located in the foothills of the Hudson Valley, nestled between the picturesque Mt. Eve and Mt. Adam. After we enjoy a tasting of wines & ciders, grab some delicious fare from the bakery cafe’, run by a CIA-trained chef and settle in for a day of The Dead.

The Gratetful Dead wrote 36,086 songs, did you know? They performed 2317 concerts in 298 different cities. Over the length of their career, the Dead have performed for more people than any band in history. The average “true” Deadhead spent over $2,000 on concerts and travelled over 3,000 miles over the past three decades. Were you one of those road trippers? It’s time to trip again…

Event Details

  • Departure Time: 8:00 AM
  • Return Time: 7:00 PM
  • Departure & Return Location: NE Corner of 73 & Broadway (1, 2, 3 to 72nd St.)
  • Bring: Your lunch and 2 liters water (minimum per person) in a backpack or hip pack; extra money to buy bottles of wine and food at the winery if you wish. Blanket or towel to sit on.
  • Included in price: Admission to Greatful Dead Tribute and Wine Tasting

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Intensity Levels

This event or trip is Intensity Level 3.

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

    Up to 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 High Ropes Climbing

High Ropes Climbing

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 Canoe & Kayak

Singles Canoe & Kayak

Other Trips in This Category

  1. 3rd of July Hike & Swim
  2. 4th of July Hike & Swim
  3. Adventure Tri Clinic
  4. Autumn Glider Soaring
  5. Autumn Mohonk Scramble Challenge
  6. Autumn Waterfall Canyoneering
  7. Awosting Falls
  8. Backcountry Snowshoe on Russian Bear Mountain
  9. Backwoods Snow Sledding
  10. Backwoods Snowshoeing
  11. Backwoods Snowshoeing: Catskill Mountains, High Point
  12. Backwoods Snowshoeing: Catskills, Panther Mountain
  13. Backwoods Snowshoeing: Catskills, Slide Mountain
  14. Backwoods Snowshoeing: Surebridge Mountain
  15. Bearfort Mountain Hike
  16. Black Ash Mountain Hike
  17. Black Rock Hike
  18. Breakneck Ridge Hike & Scramble
  19. Breakneck Ridge Hike to Mount Taurus
  20. Bullets, Beer & BBQ
  21. Canoe & Kayak
  22. Canopus Lake Hike
  23. Castle Ruin Hike
  24. Catskills Hike & Rappel: Panther Mountain
  25. Catskills Hike: Indian Head Mountain
  26. Catskills Hike: Panther Mountain
  27. Catskills Hike: Slide Mountain
  28. Catskills Hike: Sugarloaf Mountain
  29. Catskills Snowshoeing & Rappelling
  30. Class V Whitewater Rafting
  31. Clay’s Private Rock Climbing, Hiking & Camping Weekend
  32. Columbus Day 6 Mile Hike: Gertrude’s Nose in Minnewaska
  33. Corporate Horseback Riding & Wine Tasting
  34. Cross Country Ski & Snowshoe
  35. Diamond Mountain Hike
  36. Dog, Beach & Vine
  37. Echo Lake Hike
  38. Empire Hotel Rooftop Cocktails & Gear Raffle
  39. End to End: Sterling Ridge Hike
  40. Evening Horseback, Hayride & Cookout
  41. Fall Foliage Hike, Apple & Pumpkin Picking
  42. Fall Foliage Horseback, Apple & Pumpkin Picking
  43. Fourteen Peaks Hike
  44. Fourth of July Skydiving!
  45. Full Moon Halloween Hike
  46. Full Moon Hike
  47. Full Moon Kayaking to Abandoned Castle
  48. Gertrude’s Nose 6 Mile Hike in Minnewaska
  49. Groundhog Day Hike: Russian Bear
  50. Gunks Hike & Whiskey Tasting
  51. Gunks Horseback Riding & Whiskey Tasting
  52. Gunks Winter Hike & Whiskey Tasting
  53. Half Day Hudson Valley Biking, Hiking & Pub
  54. Halloween Costume Hike & Pub
  55. Halloween Hangover Hike: Ramapo Ridge 9 Miles
  56. Halloween Horseback Riding & Wine Tasting
  57. Hang Gliding Adventure
  58. High Peterskill Hike in Minnewaska
  59. High Ridge Hike & Yoga
  60. High Ropes Climbing
  61. Hike & Art Gallery
  62. Hike & Hound 6-Mile Hike
  63. Hike & Hound Eight Mile Hike
  64. Hike & Pilates
  65. Hike & Wine Tasting
  66. Hike The Great Escape
  67. Hike the Hamptons
  68. Hike to High Point in the Catskills Mountains
  69. Hike, Swim & Wine Tasting
  70. Hike, Swim, Wine Tasting & Grateful Dead Tribute
  71. Hike, Swim, Wine Tasting & Harvest Moon Folk Festival
  72. Hike, Swim, Wine Tasting & Johnny Cash Tribute
  73. Hike, Wine & Charcuterie Tasting
  74. Hike, Wine & Fondue Dinner: Appalachian Trail
  75. Hike, Wine & Fondue Dinner: Ship Rock Ridge
  76. Hike, Wine & Fondue Dinner: Tom Jones Mountain
  77. Hike, Wine & Fondue Tasting: Tom Jones Mountain
  78. Hike, Wine & Shakespeare in the Orchard
  79. Hike, Yoga & Swim
  80. Hippo Rock Hike
  81. Hollywood Stunt Class: High Falls
  82. Hollywood Stunt Class: Trampoline
  83. Horseback & Art Gallery
  84. Horseback & Hike
  85. Horseback Riding & Wine Tasting
  86. Horseback Riding and Introduction to Polo
  87. Horseback, Hike & Swim
  88. Horseback, Wine Tasting & Apple Picking
  89. Hot Air Ballooning
  90. Hudson Half Day Sailing & Hike
  91. Hudson River Brunch Sailing Excursion
  92. Hudson Sailing & Hike
  93. Hudson Valley Biking, Hiking & Pub
  94. Ice Climbing
  95. Indoor Rock & Pints
  96. Indoor Rock Climbing
  97. Intro to Backpacking & Wine Tasting Weekend
  98. Intro to Dragon Boat Racing
  99. Iron Mine & Lemon Squeezer Hike
  100. Kaaterskill Falls Eight Mile 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 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.

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