Happy Trails Guiding, LLC

Happy Trails Guiding, LLC The Berkshires premier outdoor guiding service A full-service outdoor adventure guiding service located in the heart of the Berkshires of Western Massachusetts.

Activities include mountain biking, road cycling, hiking, backpacking, walks, kayaking, canoeing, snowshoeing, xc skiing, downhill skiing, telemarking, snowboarding, fishing, unicycling and kite flying.

07/17/2025

It’s happening…

09/20/2024

The weekend is fast approaching and the weather is looking primo for a bike fest! You would not believe the amount of work that has gone into the trails at Balance Rock State Park in the past two weeks to get them ready for you to ride. Are YOU ready?

Party tents go up tomorrow as well as the floating bridge across the pond. You heard that right, a floating bridge across the pond. We ask that you have your eBike below a 10% charge when crossing to keep the frogs and fish from getting electrocuted. Just kidding, there will be a dedicated bubble bike for you to ride across on so you don't have to repack your waterlogged bearings. You may be good at crossing skinnies but have you ever tried a janky pallet bridge?

We have made some changes based on the low registration numbers so far but don't you worry, the people that do show up will be treated right and will be having a grand old time. There will not be food trucks as planned but there will be Odin's Pizza on Friday night and Old Man Jeff's BBQ on Saturday night. Kegs...check. Bouncy house...check. Disco tent...check. Pump track...check. Hoopla Olympics...check. Big ass bonfire...check. Short track races...check. Tequila Hill...check mate!

So pack up your tent, pump up those tires and get ready to Hoopla!

Schedule of events:

Friday:

2:00pm Gates open at Ponderosa Pines
3:30pm Group rides
6:30pm Pizza slinging
7:30pm Bonfire

Saturday:

8:30am Pancake breakfast
10:30am Group rides
3:30pm Pump track demo
4:30pm Floating bridge contest
5:30pm OMJ BBQ
6:30pm Live music
7:30pm Bonfire

Sunday:

8:30am Pancake breakfast
10:30am Group rides
11:30am Short Track races

02/27/2023

Good times on the trails! This was part one of a double header today, I’ll say it now, the fat biking was better than the skiing! Django & Osa love playing together.

12/14/2022

At the summit of Mount Greylock with Scout the Dog—one of the beautiful locations in our Berkshires. Want to know where to hike any time of year? Check out Berkshire Magazine’s Fall/Winter Outdoor Rec 413. The link is in our bio. And join Odin Adolphson with Happy Trails Guiding, LLC, who provided this image, as he guides us through his favorite places to hike in the Berkshires.

Have you checked out Devil’s Path yet? It’s one of 4 new trails that we built on the mountain to add to the mix.
06/29/2022

Have you checked out Devil’s Path yet? It’s one of 4 new trails that we built on the mountain to add to the mix.

It’s done! Happy Trails started building new trails at Windham Mountain Bike Park last October and through trials and tr...
06/17/2022

It’s done! Happy Trails started building new trails at Windham Mountain Bike Park last October and through trials and tribulations we have finally wrapped the project. Photos will not do it justice so the only way to experience them is to come ride them! Opening day is tomorrow and if you’d like to come test them out Happy Trails will help you with a lift pass. Moving giant boulders with the power winch, scratching the rocky terrain looking for good dirt, enduring snow squalls and mean looking bears were part of the norm as we gave it our all up there! Shout out to the hardest working crew:

05/24/2022

“No woman, no cry” - Bob Marley

“No shoes, no problem” - Kai Reed

05/22/2022

Magic rock bars!

Happy Trails to you! If you are reading this you’ve just entered the domain of dirt. We’d like to show off some recent p...
05/21/2022

Happy Trails to you! If you are reading this you’ve just entered the domain of dirt. We’d like to show off some recent projects and also the Windham Mountain Bike Park build that will be completed in time for Opening Day on June 18th.

12/14/2021

Where is all the water? No problem, Pheenix says we can still go fishing!

01/09/2021

Reporting from the frozen field -

October Mountain State Forest 1/9/21

Address

Pittsfield, MA
01201

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