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Amazing Fall Hikes in the Berkshires

Rated 5.0 out of 5 from 8 reviews.Great Barrington, United States

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Experience hosted by Mark

3.5 hours
Includes food, equipment
Up to 8 people
Hosted in English

What you'll do

This wonderful experience will begin by meeting at a local grocery store where supplies can be picked up. You will then follow me to the secret trail head (shhhhh). After some warm ups and introductions we will embark on our hike (3 hour) where you can expect the first 45 minutes to be mostly incline but moderate. We will then connect to the Appalachian Trail and continue to the top of Race Mountain for some of the BEST views in the entire Berkshires. These are breath-taking. Lunch/Snacks will be broken out and time can be spent resting, taking photos are chatting. This is the halfway point.

From here, will we hike along the ridge for more incredible Foliage views and eventually return to the magical hemlock forest. Along the way integrating some Forest Bathing techniques like "walking in Forest Time" and a "Sit Spot". Walking a little further will bring us to a beautiful pond (Plantain Pond) for the option to wash up (weather permitting). This refreshing time will feel wonderful as we make our way back down the mountain to our cars. The stroll back to our parking is easy and wonderful for conversation and reflection on our amazing hike.
This wonderful experience will begin by meeting at a local grocery store where supplies can be picked up. You will then follow me to the secret trail head (shhhhh). After some warm ups and introductions we will embark on our hike (3 hour) where you can expect the first 45 minutes to be mostly incline but moderate. We will then connect to the Appalachian Trail and continue to the top of Race Mountain for some of the BEST views in the entire Berksh…

Mark's commitment to safety

This host has committed to Airbnb’s COVID-19-related safety and cleaning guidelines – including adhering to social distancing guidelines, practising good hygiene, and ensuring that all participants wear a mask.
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What's included

  • Food
    I will have some snack bars and trail mix if you didn't carry enough.
  • Equipment
    I will have an extra set of Hiking Poles. I will always carry First Aid, Bu...
From ₹4,922
/ person
No dates available

Meet your host, Mark

Host on Airbnb since 2013
  • 8 Reviews
  • Identity verified
I've lived in the Berkshires for nearly 20 years. I walk the Berkshire Hills through all 4 seasons and find hiking a spiritual experience or deep connection to self and the planet. I have trained as a Mindful Outdoor Leadership Guide and Wilderness First Aid. I lead outdoor experiences for well known Health Centers in the area to include Kripalu and Miraval/Cranwell.

I have hiked stretches of the A.T. (East) and John Muir Trail (West). My other love is photography and spend hours in nature taking photos. I can also be found teaching Yoga, Meditation and Trauma-Informed therapies to include those pertaining to Addiction Recovery.
I've lived in the Berkshires for nearly 20 years. I walk the Berkshire Hills through all 4 seasons and find hiking a spiritual experience or deep connection to self and the planet. I have trained as a Mindful Outdoor Leadership Guide and Wilderness First Aid. I lead outdoor experiences for well known Health Centers in the area to include Kripalu and Miraval/Cranwell.

I have hiked stretches of the A.T. (East) and John Muir Trail (West). My other love is photography and spend hours in…
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Where you'll be

Our hike takes us along the Appalachian Trail in Sheffield MA. up to Race Mountain. We will have the option to swim at Plantain Pond. We will be able to see not only Massachusetts but Connecticut on this hike. Some of the most amazing views in the Berkshires are on this special hike.

Rated 5.0 out of 5 from 8 reviews.

Erin
August 2019
I took my son on this 3 hour hike with Mark and it was amazing. Mark made us feel comfortable from the beginning. He told us what to expect and prepared us for the entire experience. Took us to a place and on a route we would not have found ourselves. We loved it, the sounds and sights of the forest as well as the breathtaking views from the Appalachian trail.
I took my son on this 3 hour hike with Mark and it was amazing. Mark made us feel comfortable from the beginning. He told us what to expect and prepared us for the entire experie…
Ruth
August 2019
Hiking with Mark was a phenomenal experience. So much more than a hike (and that alone is extraordinary), Mark shared interesting and insightful information about the forest and the area. Mark is also super easy to reach and communicate with and he was more than willing to accommodate my interests and schedule. The views were incredible, the trail and forests lovely. Don't hesitate for a second if you're looking to hike with someone who is knowledgeable about the area and eager to share what he knows. He's also a genuine, warm and kind person. I will absolutely contact Mark again next time I'm in the area.
Hiking with Mark was a phenomenal experience. So much more than a hike (and that alone is extraordinary), Mark shared interesting and insightful information about the forest and th…
Veronica
July 2019
Mark provided wonderful experience for us today. He was able to guide us on the most beautiful hike with gorgeous views while teaching us about the power of nature. He used his knowledge of meditation and mindfulness & very nicely integrated into our hiking experience. We highly recommend it! Thank you Mark!
Mark provided wonderful experience for us today. He was able to guide us on the most beautiful hike with gorgeous views while teaching us about the power of nature. He used his kno…
Kelley
July 2019
Mark is a fantastic guide and local expert in outdoor leadership and how nature impacts your health and wellbeing. I am sure he can go beyond the Berkshires to deliver a world class experience like he did for us. For example, he knew about the timing of the blooms for Moutain Laurels and he created an experience around the magic of that fauna,, and as we ascended into the higher elevations, he described a bit about what we were going to see so that we did not miss it and could experience the anticipation of what was to come. From fern laden lower level to rock terrain and a flat exposed summit to take it all in, the hike revealed the beauty of the Berkshires. There is NO WAY you could experience this on your own. My mantra is "where there is beauty I want to be there"...and I was right in the middle of it thanks to Mark's expert, friendly, insightful and fun approach to hiking. I am not a serial hiker, just like to hike as one of the things I do to stay fit and engaged in the mind body communities around the world.
Mark is a fantastic guide and local expert in outdoor leadership and how nature impacts your health and wellbeing. I am sure he can go beyond the Berkshires to deliver a world cl…
Andrea
July 2019
From beginning to end Mark made this a magical experience for me and my husband. Of course, he did get a little help from the Mountain Laurel that were in peak bloom (which only lasts 7-10 days) turning many otherwise green corridors into pathways that were covered with white and pink blossoms! But spectacular scenery aside, Mark is an incredibly talented and gifted man who brought his military training as a search and rescue trainer for the US Air Force, his expertise and knowledge of the flora and fauna and backwoods trails, as well as his knowledge as a certified therapist for those with PTSD -- all of which made for a truly memorable 3+ hours on July 4th that we won't soon forget. While the hike was not as strenuous as we expected, the views from Race Mountain over the valley in western MA and across the mountains into Connecticut exceeded our expectations! When we stopped to admire the view Mark shared a container of delicious blueberries and raspberries ...another special moment. And when we resumed the hike, wouldn't you know it, we stumbled across bushes of sweet wild blueberries that were still warm when we popped them in our mouths! We are kicking ourselves that we didn't bring our swimsuits to enjoy a dip in Plaintain Pond -- so if you go, remember to bring something to swim in with you! There's even a beautiful green screen that you can change behind. Even though we've been coming to The Berkshires for 20 years, this was a hike we would have never found on our own! Thank you Mark for such a special July 4th.
From beginning to end Mark made this a magical experience for me and my husband. Of course, he did get a little help from the Mountain Laurel that were in peak bloom (which only l…
Indi
July 2019
Our hike with Mark was the highlight of our trip to the Berkshires. He expertly led us on a hike that there is no way we would have been able to do without his guidance. It felt like we were engaging in something only locals would know about. He is thoughtful, compassionate and highly knowledgeable. It was an exhilarating adventure that allowed us to deeply enjoy nature and our Berkshire surroundings... which are so different from life in the city. The views were stunning. Our one regret was not being able to do more hikes or forest bathing during this trip. Book this experience with confidence! Our time with Mark was absolutely amazing!
Our hike with Mark was the highlight of our trip to the Berkshires. He expertly led us on a hike that there is no way we would have been able to do without his guidance. It felt li…

Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note that outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Government ID

You’ll need to take a picture of yourself that matches the photo on your ID. This is so Airbnb can confirm who’s actually going on the experience. You’ll only have to do this once.

Guest requirements

Up to 8 guests ages 18 and up can attend.

More tips

Please let me know if you have any special needs or concerns when we are discussing out excursion. I can be somewhat flexible with our timing and support equipment.

What to bring

Bring proper shoes for Fall hiking. A warm layer of clothing. Maybe warm tea.

Bring your own Lunch / Snacks and Water please