What we're about

Welcome to Hiking Boots & Booze!

Don't be deceived by the name! Hiking Boots & Booze is a dedicated hiking and adventure group, but we always end each event--or intertwine each event--with refreshments and food, and alcoholic beverages are always at your discretion. Hiking is the main event (but not always the best part), and members are not required to participate in the drink and food component afterward.

Hikes typically range between 4 and 8 miles and are concentrated across the southern Berkshires and throughout the Catskill Mountains, but may also include multi-day trips elsewhere. On all hikes we will keep a moderately quick pace, so you should be in reasonably good shape, or at least fit enough to keep the pace of the group. Safety is important and it is your responsibility to read each event description fully, along with any associated links, so that you arrive fully prepared.

**ATTENDANCE** Please be mindful of your reservations. If you commit to an event then decide not to go, please change your r.s.v.p. IMMEDIATELY so the group is not standing around waiting for you. Anyone with 2 no-shows may be removed from the group without notice.

Becoming a member of the Hiking Boots & Booze Meetup will also mean that you understand and agree with our disclaimer below.

DISCLAIMER: You are solely responsible for your safety and well-being on any event you attend. No Organizer, Host or other member of this group is in any way liable for any injury or misfortune that could occur. The Organizers and event hosts are not trained in any medical or rescue procedures, nor are they professional trail guides. Some hikes may be exploratory, meaning the Organizer or Host has not previously hiked that particular trail or trail system. You therefore agree to accept all risks when you arrive to participate in any event scheduled. As a member of this group, you agree to release the Organizer, all event hosts and fellow members of any and all liability. If you decide to separate from the group during an event, you are responsible for your own safe return. All posted hike distances, durations, elevations, and difficulty levels are estimated and may not accurately represent a particular hike or event. Any extracurricular activities associated with a posted event in which you participate in will be done at your own risk. By joining this group and attending an event, you are demonstrating that you understand you are responsible for your own safety as well as the safety of anyone who accompanies you as a guest on any event hosted by Hiking Boots & Booze Meetup.

Upcoming events (3)

North Mountain at North-South Lake + Last Chance Cafe + Jane's Ice Cream

6+ miles \ 4-5 hours \ 1200 feet hellevation gain \ 4 out of 6 beers in difficulty (moderately difficult)

This hike follows a section of the popular Catskill Mountains Escarpment trail and includes multiple overlooks of the Hudson Valley such as Artist's Rock, Lookout Rock, Sunset Rock, Newman's Ledge, North Point, and North Mountain itself. We'll return on a different trail and check out Badman's Cave before swimming the length of the lake back to our cars.

After towling off, we'll head to Last Chance Cafe in Tannersville, just 5 miles away.

Dude, I'm kidding! There's no way I'm swimming in October.

Last Chance offers about 300 different beers, a decent menu selection, comfy atmosphere, and hot mountain women waitresses. Maybe a couple waiters, too. After eats, I'm walking to Mama's Boy Burgers for a chocolate milkshake. The best I've ever had!

*Meetup isn't free for me so please consider a contribution*.

Autumn in Asheville!

Needs a location


  • Tour entire Skyline Drive & Blue Ridge Parkway during peak leaf season
  • Mount Mitchell - highest mountain east of the Mississippi
  • Blowing Rock, North Carolina
  • 3 nights in Asheville, NC
  • Biltmore Estate and winery - Largest privately-owned home in America
  • Brief hikes with amazing views in Great Smoky Mountains N.P.
  • 17 mile downhill bicycle ride along the Virginia Creeper Trail

ITINERARY - This represents my course of travel which you can replicate in part or in full or not at all.

Saturday, Oct. 15
Travel to Front Royal, VA. Hike to Buzzard Rock if time allows. Meet up for dinner. Stay overnight at Hampton Inn Front Royal

Sunday, Oct. 16
Begin traveling along Skyline Drive and pick up the Blue Ridge Parkway in Afton VA and continue to Roanoke, then check into hotel. Dinner and nightlife in Roanoke. Overnight at Hampton Inn & Suites Roanoke-Downtown VA

Monday, Oct. 17
Continue along the Blue Ridge Parkway to well-renown Blowing Rock, NC. Explore, then dinner in town. Overnight at Holiday Inn Express Blowing Rock

Tuesday, Oct. 18
More Blue Ridge Parkway with a detour to Mt. Mitchell before arriving in Asheville. Dinner and nightlife downtown. Overnight at Cambria Hotel Downtown Asheville

Wednesday, Oct. 19
Tour Biltmore Estate, gardens, and winery (be sure to reserve the "Admission + Audio Tour" for 11:30). Lunch at Biltmore Cafe. Dinner and nightlife in downtown Asheville. Overnight at Cambria.

Thursday, Oct. 20
Drive the final section of the Blue Ridge Parkway to Cherokee NC, then continue to the heart of Great Smoky Mountains National Park for an easy hike to Clingmans Dome and Mount Love along the Tennessee border. Late afternoon and evening in Asheville. Final overnight at Cambria.

Friday, Oct. 21
Depart Asheville for Damascus VA, rent bicycles and enjoy an easy 2-3 hour, mostly downhill ride along a scenic brook. Lunch in Damascus. Overnight in Roanoke VA at Hyatt Place Roanoke Airport/Valley View Mall.

Saturday, Oct. 22
Travel home

THE TRAVELERS (who's going and how):

- Dale, and probably Gary, are riding with me
- Joan is driving herself, although now has a potential conflict
- Donna and Kara are flying individually into Roanoke Sunday, renting a car, then driving in tandem with me and Dale.
- Nicole and her sister Jackie will connect with us in Roanoke, have their own car, and might or might not stick with the group
- Chrissy is flying into Asheville Tuesday, renting a car, and meeting us at Mt. Mitchell around noon before we all make our way to Asheville.
- Craig is flying into Asheville Tuesday around noon.

Finger Lakes 2023!

Needs a location

Join us for another long weekend in Watkins Glen on Seneca Lake! We'll be staying an extra day this time so you'll have more time to do more stuff, or to relax, and I've again reserved the entirety of Admiral Peabody's Lakeside Lodging. Cost for Peabody people is $350 for 4 nights.

I wish everyone could fit at Peabody's, but it's just not possible. As an alternative, the Anchor Inn is a great place just a half mile down the road, and they have a tiki bar. If you already know you want to stay at the Anchor Inn you can call and get on a waiting list, but they're not booking reservations until March. Several other options are available as well.

Regardless of accommodations, everyone goes on the Waitlist here and I'll move people to the Going side once I contact you about Peabody's, or you tell me you've booked (or are on a waiting list) elsewhere.

I'll have a few activities planned during the trip, but mostly you're on your own, and you won't have any trouble finding things to do, especially if you like chasing wineries, breweries or distilleries.

It is your responsibility to follow the comments here for any updates between now and the end of the trip.

Off-site guests visiting Admiral Peabody's should park on the lake side of the road since parking onsite is limited.

Prospective Itinerary:

Check-in after 3 PM, dinner on your own

9:30 AM - Meet at Treman State Park for a 4.3 mile hike
6 PM - All-group dinner at Peabody's. Details later

9:30 - Meet at Watkins Glen State Park for a 2.6 mile hike

9:30 - Meet up to carpool to Keuka Lake wineries and have lunch and ice cream in Hammondsport

Check out by 11:00


Photos (4,486)