Skip the route mapping and heavy packing. We provide the daypacks, poles, and trail snacks.
AUGUST 16, 2026
Escape to Mount Kearsarge South.
Whether you’re lacing up boots for the first time or you’re a seasoned hiker craving a zero-planning escape, we handle the driving, the gear, and the logistics. You just bring your sense of adventure.
A Full-Service Adventure. Zero Planning Required.
Located in Wilmot, NH, Mt. Kearsarge (South) is a 2,937-foot peak on the “52 With A View” list, boasting a rare 2,100-foot prominence. Derived from the Pennacook word Carasarga, the mountain is hiked via the Barlow and Winslow trails. The Winslow trail honors Admiral John Winslow, commander of the USS Kearsarge—a historic Civil War ship built from the mountain’s timber that famously sank the Confederate Alabama.
The Ultimate Adventure For All Hikers
Getting into the mountains for the day shouldn’t feel like a part-time job. We take the friction out of the outdoors so you can focus entirely on the experience, the views, and the camaraderie.
No fighting for trailhead parking or dealing with traffic. Just sit back and relax in our Sprinter van.
Our expert guides navigate the terrain, share local history, and build a welcoming trail community.
Who is This Hike For?
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Beginners & Families: With its approachable distance and gentle pacing, this is the perfect starting line for new hikers and families looking for a safe, highly rewarding mountain experience.
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Solos, Couples & Groups: Whether you’re flying solo and want to meet new friends, or a couple looking for a memorable outing without the stress of planning, this trip is built for effortless connection.
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Experienced Trail Vets: Even seasoned hikers book with us for a full-service escape. Leave the driving, logistics, and heavy lifting to us while you simply relax and enjoy a hassle-free day in the Whites.
Hike Overview
Book Your Hike – $249Beginner
2.91 mi
1,138 ft
3.5 hrs
53:40 min/mi
Date
August 16, 2026
Pickup Locations
- Alewife Station | 5:30 AM
- North Station Garage | 6:00 AM
- Andover | 6:30 AM
Itinerary (transportation included)
- Final Pickup | 6:30 AM
- Rest Stop | 7:15 AM
- Arrive at Trailhead | 8:30 AM
- Start Hike | 8:45 AM
- End Hike | 2:45 PM
- Arrive back at Closest Dropoff** | 5:15 PM
*times are estimates and will vary based on group pace and traffic conditions.
**Dropoffs are roughly 30 minutes apart, and will vary based on initial pickup locations
Cost
$249
Meet Your Guide
Dave
A lifelong New Englander and former finance professional, your guide Dave traded twenty years behind a desk for a life on the trail. After a post-pandemic realization that his true expertise lived in the mountains, he stepped away from the corporate world to turn his passion for the outdoors into a hands-on mission to lead explorers like you.
On the trek, Dave is dedicated to providing expert support, creating a safe, ethical, and welcoming environment where you can comfortably push your limits and forge genuine connections with your fellow hikers. When he isn’t out leading your next adventure, you will most likely find him spending time with his family or sharing stories around a campfire.
Favorite Hike
Nineteen Mile Brook Trail
Favorite Hiking Gear
Shoulder Strap Pocket
City-to-Summit Access: What’s Included
Your $249 ticket covers your entire day from Boston to the summit and back.
Book Your Hike – $249Door-to-Trail Transport
Round-trip transportation in our comfortable Sprinter van from Alewife, North Station, or Andover.
Premium Gear
High-quality daypacks, trekking poles, and trail essentials provided for the day.
Fuel for the Journey
Curated trail snacks and hydration solutions are included with every booking.
Expert Guides
An expert guide to manage the pacing, share wilderness skills, and facilitate an unforgettable day.
Safety as a Standard
Every guide is Wilderness First Aid and CPR/AED certified.
Meaningful Connections
A trip designed for building community with others and sharing mountain memories.
Frequently Asked Questions
Find all the details you need to prepare for your journey and hit the trail with total confidence.
Book Your Hike – $249You don’t need to be a mountaineer, but you do need a solid baseline of fitness. Covering 12 miles and 4,300 feet of elevation gain over rocky, uneven White Mountain terrain is a serious physical challenge. If you regularly hike, run, or do endurance workouts, you’ll do great! We hike at a supportive, group-friendly pace—nobody gets left behind.
Absolutely not. We hike at a supportive, conversational pace, take plenty of breaks for photos and water, and nobody gets left behind. This specific hike is our most approachable trail, making it perfect for beginners and anyone looking for a relaxed pace.
Yes! Because of the shorter mileage and high reward, Mount Kearsarge is a great option for adventurous older kids and teens. (Please contact us directly if you plan to bring children under 12 so we can ensure the gear sizing and pacing will be a fit).
We provide the daypacks, trekking poles, and snacks! You just need to wear comfortable, moisture-wicking athletic clothing (avoid cotton), broken-in hiking shoes or sturdy trail runners, and bring your own water bottles. We will send you a simple “what to wear” guide as soon as you book.
Yes! While our Sprinter van transport from Boston is a huge perk, you are more than welcome to drive yourself and meet our group and guides right at the trailhead at 8:30 AM.
We hike rain or shine! Mountain weather is famously unpredictable, which is exactly why having a certified, expert guide is so valuable. We will only alter the route or cancel the itinerary if conditions become actively unsafe (such as severe thunderstorms or extreme winds).
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