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Grayson Highlands Backpacking: 2 Days With Wild Ponies
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Redpoint travel protection
Weather shifts, flights cancel. Core and Premium include Redpoint travel protection to cover you when they do. Standard follows 57hours' booking policy. See full coverage
Every booking, whichever you pick
Cancel within 48h of booking 100% refund
Cancel 60+ days before departure (Any or no reason) 70% refund
Full coverage details
Basic Standard terms Most popular Core protection Recommended Premium protection
Cancel within 48h of booking
100% refund 100% refund 100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund 70% refund 75% refund
Cancel any time (Covered reason)
75% refund 100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p. Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p. Up to $100,000 p.p.
Basic Standard terms
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Rescue, evacuation, and medical coverage
Most popular Core protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
70% refund
Cancel any time (Covered reason)
75% refund
Cancel any time (Any or no reason)
Cancel under 60 days (Any or no reason)
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Recommended Premium protection
Cancel within 48h of booking
100% refund
Cancel 60+ days before departure (Any or no reason)
75% refund
Cancel any time (Covered reason)
100% refund
Cancel any time (Any or no reason)
75% refund
Cancel under 60 days (Any or no reason)
75% refund
Travel: canceled flights, lost baggage, delays
Up to $1,000 p.p.
Rescue, evacuation, and medical coverage
Up to $100,000 p.p.
Cancellation policy

The percentages in the table above are of the full trip price, not of what you’ve paid at the time of booking.

Cancellations made within 48 hours of booking receive a full refund on all plans, including booking fees and insurance. After the 48-hour window, your refund depends on your selected protection plan and when you cancel. Core and Premium plans extend your cancellation rights beyond the Standard policy:

  • With Core, a covered reason gets you 75% of your trip cost back — even the day before you go.
  • With Premium, a covered reason gets you 100% of your trip cost back — and any other reason gets you 75%, right up to the day you leave.
What counts as a covered reason
  • Sudden illness or injury — yours, a travel companion’s, or an immediate family member’s, confirmed by a doctor
  • Death of a traveler or an immediate family member
  • A natural disaster affecting your destination or your departure point
  • A government travel advisory against travel to your destination

Changing your mind isn’t a covered reason. Premium is the only plan that covers that. Documentation is required for all insurance claims.

Everything the travel insurance covers

Both plans include travel insurance through Redpoint Travel Protection. Core insures 75% of your trip cost; Premium insures 100%.

Maximum per person:

  • Trip cancellation — up to 100% of your trip cost
  • Cancel for any reason — up to 75% of your trip cost (Premium only)
  • Trip interruption — 150% of the trip cost limit
  • Trip delay — $200 a day, $1,000 max
  • Itinerary change — $250
  • Single occupancy supplement — up to 100% of trip cost
  • Missed connection — $1,000
  • Travel inconvenience — $250 each, $750 max
  • Pet return — $1,000 per pet
  • Baggage and personal effects — $2,500, max $300 an item
  • Baggage delay — $600, after 12 hours
  • Baggage delivery — $100 per trip
  • Emergency medical expenses — $100,000
  • Medical evacuation and repatriation — up to $1,000,000

These are maximums. What a claim actually pays depends on what you can document and on the policy’s exclusions — pre-existing conditions and undeclared activities among them. We’ll send the full policy wording with your confirmation.

Reserve deposit (30%) $0
Second Payment Amount: $0
Grayson Highlands Backpacking: 2 Days With Wild Ponies
Itinerary
Grayson Highlands Backpacking: 2 Days With Wild Ponies
Date(s)
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Number of travelers
1 Person
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The Dyrt pro camping app free for 1 year
  • Two days, one night, and 9 mi (14.5 km) of hiking split across them, so nobody's rushing. We meet at the overnight backpackers lot in Grayson Highlands State Park, fit and share out the gear, then hike up into the balds with rocky outcrops and long mountain views the whole way. Camp goes up in the backcountry, dinner is a warm dehydrated meal, and the evening is for sunset and conversation. Day two starts with coffee and time to look for the ponies before we pack up and walk back out. All meals are included, and the group stays small at seven guests maximum.

    • We meet at the overnight backpackers lot in Grayson Highlands State Park, where your guide hands out food for the trip and fits everyone with packs, tents, trekking poles, and sleeping pads. Shared gear like stoves, water filters, first aid supplies, and the bathroom kit gets split among the group, so nobody carries too much. Then we head out at a relaxed pace through rolling grassy balds and past rocky outcrops, with long mountain views and plenty of stops for photos. Keep an eye out for the wild ponies that roam this area. We reach camp in the afternoon, set up tents together, cook a warm meal, and watch the sun drop behind the ridges.

      Meals: All meals provided
      Accommodation: Two-person backpacking tent at a backcountry camp

      Two backpackers hike over rocky ground through a grassy, shrubby highland with forested hills behind in Richmond
    • Coffee comes first, brewed right at camp while the highlands wake up around us. We eat breakfast, pack up our gear, and practice leaving the site cleaner than we found it. The hike back gives us one more chance to spot the free-roaming ponies grazing across the balds, and we take our time with the wide-open views and the rocky outcrops along the way. Your guide is there for any last questions about gear, packing, or where to go on your next trip. We finish at the overnight backpackers lot, return the loaned gear, and say our goodbyes. Total for the two days is 9 mi (14.5 km) round trip.

      Meals: Breakfast
      Distance: 9 mi (14.5 km) round trip over two days

      Morning coffee, pony spotting, and hike back to the trailhead — Hiking in Richmond
    • Included:

        • An experienced, local backpacking guide with extensive knowledge of the area (Wilderness First Responder certified)
        • 2-day backpacking trip in Grayson Highlands, Virginia (2 days of hiking, 9 mi / 14.5 km round trip)
        • Accommodation for 1 night at a backcountry camp (two-person backpacking tents)
        • All meals on trail, with a selection of lightweight backpacking-friendly options including dehydrated meals, snacks, and drinks (coffee included), distributed the morning of your trip
        • Personal backpacking gear: backpack, tent, trekking poles, and sleeping pad
        • Shared group equipment divided among the group: stoves, water filters, first aid supplies, and bathroom kits
        • Gear fitting and distribution at the trailhead before you hit the trail
        • Intro to backpacking instruction, covering packing your bag, setting up camp, and using your gear
        • A detailed, trip-specific packing list and route-specific water guidelines sent after booking

      Not included:

        • Transportation to Grayson Highlands State Park, Virginia
        • Pre-trip lodging (Damascus, VA is a nearby option)
        • Sleeping bag and the other personal items listed under “What do I need to bring?”
        • Anything not mentioned in the ‘Included’ section above
        • Insurance — recommended, available at checkout
        • Guide gratuities — optional
    • In order to join this Grayson Highlands backpacking tour, good fitness is required as well as no prior backpacking experience. The trip covers 9 mi (14.5 km) round trip split across the two days, so the mileage stays approachable while you carry a pack.

      While this trip is beginner-friendly, we do recommend having a regular fitness routine in place. Hiking with a pack is a rewarding but physically challenging experience! To help ensure you’re prepared, a training plan is provided after booking.

      Your guide fits and distributes gear before you set off, and shared items like stoves, water filters, and first aid supplies are divided among the group so no one carries too much. Terrain is rolling highland balds and rocky outcrops, and the pace is relaxed with plenty of stops for photos and pony spotting.

      Looking for more inspo? Discover our collection of hiking adventures in US National Parks!

    • Your guides provide the bigger items, so your backpack, tent, trekking poles, and sleeping pad are all taken care of. Here’s what to pack yourself. After booking, your guide will send a full packing list specific to your trip, including water guidelines for the route.

      Gear:

        • Sleeping bag (a 20-degree bag is recommended in April, May, September, October, and November; the mountains get chillier than you’d think)
        • Headlamp
        • Mess kit
        • Water bottles or bladder, 3 liters recommended, with one in a heat-safe container such as a Nalgene so you can use it as a hot water bottle on cold nights

      Clothing & footwear:

        • Hiking boots or shoes
        • One outfit to hike in and one to sleep in (no need for extra changes of clothes)
        • Adequate layers for the weather, avoiding cotton where possible since it stays damp and cold once wet
        • Rain gear: rain jacket and rain pants

      Other:

        • Any personal medication
        • Toothbrush and toothpaste, the only toiletry really needed out there

      Most everyday luxuries aren’t needed in the backcountry, so feel free to leave makeup, deodorant, and similar products at home. Extra electronics and entertainment can stay behind too; this is a good chance to go screen free and enjoy nature.

      Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

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    • Group sizes and pricing:

        • It takes a minimum of 3 people for this Grayson Highlands backpacking tour to operate. The maximum group size is set at 7 participants.
        • If the minimum number of hikers isn’t met, your guide will reach out within 2 weeks of your trip date.
        • Solo travelers are very welcome on this trip. You can have a two-person tent to yourself or share with another participant to lighten your pack, at no extra cost either way.
        • Grayson Highlands backpacking tours can be arranged for larger groups, contact us to make arrangements.

      Min. age requirements:

        • If you are older than 18, you’re good to go.
        • Minors younger than 18 may be permitted to join the Grayson Highlands backpacking tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.
        • If your group has participants under the age of 18, contact us prior to booking to make arrangements.
    • Yes! Solo travelers can have a two-person tent to themselves at no extra cost, or share one with another solo traveler to lighten their packs. You can note down your preference at checkout.

    • The starting point of your Grayson Highlands backpacking tour is the overnight backpackers lot in Grayson Highlands State Park, Virginia. Most people drive or rent a car to get there, and the exact address and directions will be sent to you after booking.

      Looking for somewhere to stay the night before? Damascus, VA is nearby and a popular option, though pre-trip lodging is not included in this trip.

    • We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

      Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

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