Outdoor Explorers Club
Ages 8 - 14 • $50.00 / hike
Financial Aid available
Follow the call of adventure into the mountains of the Berkshires! With an expert mountaineer and naturalist to introduce you and your team to the geology, wildlife, and hidden history along the way, you’ll visit plunging waterfalls, serene mountain lakes, and cloud-high summits with hundred-mile views. Each all-day hike is a new challenge that offers new rewards to win: new friends, new skills, new stories, and new triumphs that prove just how far you’re able to go.
Meet Your Guide
Jeramy Vallianos is a Berkshires native who started learning with Flying Cloud as a child, and has been leading hikes and programs with us since 2010. A professional mountain guide and Wilderness First Responder, Jeramy has led hiking adventures for kids all over North and South America. He currently works for the World Leadership School, guiding backpacking school groups through the Andes Mountains. He lives in Patagonia with his wife and son, building a new rural homesteading community with native Argentines, but he returns to his home mountains each summer to join Flying Cloud Institute in our Berkshires adventures.
Where We are Going
Alander Mountain
A longer trail that rewards the steep final climb with some of the most spectacular views in Western Massachusetts.
Date: Saturday, July 12, 2025. (Rain Date: Sunday, July 13, 2025)
Drop-off Time: 9:00 am at the Trailhead
Pick-up Time: 3:00 pm
Trailhead: Mount Washington State Forest Headquarters
162 East St., Mount Washington, MA 01258
Distance: 5.8 miles out-and-back
Total Ascent: 1,821 feet
Difficulty: Strenuous. (Gentle for first 0.8 miles, Moderate for next 1.1 miles, and Steep for final 1.0 mile.)
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Mount Everett Summit via Guilder Pond
A hike to the summit of the Taconic Range’s tallest peak, with a pleasant, easy loop around an iconic mountain pond at the midway point.
Date: Saturday, July 19, 2025. (Rain Date: Sunday, July 20, 2025.)
Drop-off Time: 9:00 am at the Trailhead
Pick-up Time: 4:00 pm
Trailhead: Across from 399 East St.,
Mount Washington, MA 01258
Distance: 4 miles out-and-back, with a loop around Guilder Pond.
Total Ascent: 954 feet
Difficulty: Strenuous. (Moderate climb for 0.9 miles, with a Gentle 0.7-mile walk around the pond, then a Steep 1.6-mile climb to the summit.)
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Mount Everett Ridgeline via Race Brook Falls
Visit one of the Berkshires’ tallest and most-beloved waterfalls, then continue climbing to the ridgeline of the mountain range for the rewarding view.
Date: Saturday, July 26, 2025. (Rain Date: Sunday, July 27, 2025)
Drop-off Time: 9:00 am at the Trailhead
Pick-up Time: 4:00 pm
Trailhead: Race Brook Falls Trailhead,
South Undermountain Road, Sheffield, MA
Distance: 3.6 mi out-and-back
Total Ascent: 1,230 feet
Difficulty: Strenuous
“Difficult” (1.1 mile of Steep terrain, then 0.7 miles at slightly more Moderate grade.)
For Adult Caregivers
Outdoor Explorers Club adventures are no walk in the park! These hikes are deliberately chosen because they’re challenges, and several extra hours are built into each day’s program to ensure every child’s safety, enjoyment, and comfort. We take frequent breaks that are filled with trail games, wilderness wisdom, survival skill practice, and time for kids to engage with their natural curiosity. Most importantly, we break for rest and hydration! Led by our expert guide with decades of experience in the field, the Outdoor Explorers Club program is designed to help kids grow by letting them climb above and beyond their comfort zones. By the end of each trip, we want every member of the Outdoor Explorers Club to feel more capable, accomplished, and brave than they were before. And yes, a little sore, too.
Each adventure begins and ends at the trailhead listed. If the weather forecast calls for substantial rain or thunderstorms, you will receive an update by email and phone at least one hour before the 9 am start time. (Adventures will rarely be canceled prior to the date, as weather conditions change quickly in the summer.) If an adventure is postponed for forecasted inclement weather, the Sunday immediately following it will be the new date.
Adventures will typically return to the trailhead prior to the pick-up time to inspect for ticks and wash legs with anti-poison ivy soap, just as a precaution. However, we strongly recommend that your child shower and inspect themselves for ticks soon after the adventure.
What to Bring
Musts:
Backpack with two straps. (No draw-string bags!)
Closed-toe shoes or hiking boots. Waterproof is preferable.
Water bottles filled with at least 2 quarts of water at the start of the hike.
Packed lunch and snacks, preferably high in calories and protein. Keep in mind that paper bags may easily get wet and tear!
Thin plastic rain poncho in case of unexpected downpours.
Insect repellent.
Sunscreen with sufficient SPF.
Good Ideas:
Hiking poles, properly fitted for their height.
One dry pair of socks in a plastic bag.
Not much else! There will be little chance to use books or binoculars, and a lighter backpack will make hiking much easier.