The Berkshires Blog

This is Outdoors in the Berkshires


A blur of cycling jerseys passes along grassy meadows on a 100 mile century ride, crowds cheer paddlers leaving the water on the middle leg of one of the oldest bike-paddle-run triathlons in the country, and a fisherman with over fifty years of experience on the river teaches beginners how to cast a fly at the top of Mount Greylock — this is summer in the Berkshires. Whether you’re looking to learn, do, or watch, these summer events offer something for everyone.

Guided Full Moon Hike & Bonfire

From marshes to woodlands, to fields and orchards, Hilltop Orchards offers a generous slice of the New England landscape. You can discover all of these habitats in detail, then enjoy the glow of a bonfire and the full moon, on one of Hilltop’s guided full moon hikes, held throughout the summer. With over 200 acres to explore, expert guide Holly Brouker to lead the way, and a wine tasting as your reward, there’s no better way for an outdoor enthusiast to spend a moonlit evening in the Berkshires.

When and Where: May 25, June 22, July 20, August 17, 6:30 p.m. — Hilltop Orchards, Richmond, MA

Click here for more info. $10 per person.

100 Miles in the Saddle… Bike Saddle, That Is

First run in the 1960s, the Mount Greylock Century holds claim to being one of the oldest century rides (100 miles in under 12 hours) in New England. While a century ride is not for your everyday recreational rider, if you’re up for the challenge, the Mount Greylock Century offers a full tour of some of the most scenic roads in the region, perfectly planned food and water stops, and over 10,000 feet of climbing.

When and Where: Saturday, July 6, 7:30 a.m. — Notchview Reservation, Windsor, MA

Click here for more info. $35 early registration.

Or if you are looking for an even longer ride, check out the 4 day Berkshires to Boston Bicycle Tour which starts at Hancock Shaker Village.

When and Where: Wednesday, September 18, 10:00am – Sunday September 22, 2:00pm –Hancock Shaker Village

Click here for more info.

Learn to Cast a Fly at the Top of Massachusetts

While some of the state’s best trout waters sit 2000 vertical feet below you, it’s hard to think of a better landscape to learn the basics of fly fishing – the forward cast and roll cast – than the top of Massachusetts’s highest peak, Mount Greylock. Among a packed list of events held at the Bascom Lodge at the mountain’s summit (don’t worry, there’s a paved road to the top), the Fly Casting Workshop, lead by Fred Moran, is one of the most unique. Fred brings with him over 50 years of fly fishing and teaching experience. And though a river may not run through it, the open meadows atop Greylock are perfect for casting practice (with a good possibility of learning how to cast in the wind). If you’ve ever wanted to learn the art of casting a fly (or cast better), join in the fun at the Bascom Lodge on August 3!

When and Where: Saturday, August 3, 3 – 5 p.m. — Bascom Lodge, Mount Greylock State Reservation, Adams, MA

Click here for more info. Free!

Bike, Paddle, Run! Elite Athletes and Fun-Seeking Amateurs Compete Side-by-Side

Arguably the crown jewel of active events in the Berkshires, the Josh Billings RunAground Triathlon returns for its 37th year on the last Sunday of summer, September 15. With the renowned 19th century humorist as its namesake, “the Josh” is one of the largest and oldest bike-canoe-run triathlons in the country and has become known for its lighter side of competition. Competitors will find over 40 different race categories to choose from, varying on age, gender, team size, and type of watercraft (canoe, kayak, or paddleboard), plus there’s a free kids running race on Sunday afternoon.

“The Josh” is a “don’t miss” for spectators as well. Watching from any one of the points along the 27 mile bike, 5 mile paddle, or 6 mile run, allows you to catch elite competitive athletes and fun-seeking amateurs at the top of their game.

When and Where: Sunday, September 15, 9:30 a.m. — Great Barrington, Stockbridge, Lenox, MA

Click here for more info. Entry fees vary. 

Honorable Marathon Mention

I already profiled the 4th Annual Memorial Day Marathon Races in my BMR Blog for spring events, but I can’t leave this newsletter without mentioning this awesome weekend of races. Click here for more on the Marathon Races.

When and Where: Saturday & Sunday, May 25 – 25, 8 a.m.  — Great Barrington, Stockbridge, Lenox, MA