What we're about

Welcome to Hiking Boots & Booze!

Don't be deceived by the name! This is a serious hiking and adventure group, but we always end each event with refreshments and food, and this is at your discretion. Hiking is the main event (although often not 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 through the Catskill Mountains, but also include multi-day trips elsewhere. On all hikes we will keep a moderately quick pace, so you should have some hiking experience, or at least be 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 come 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)

Macedonia Mountain Laurel + Pavilion Party

Needs a location


7 miles \ 4-5 hours \ 1700 feet hellevation gain \ 5 out of 6 beers in difficulty

This is a combined event with Shawangunk Hikers so we'll likely split into two or even three hiking groups. You can sign up here then pick your hike the day of the event.


Restroom, electricity and running water onsite

Please post what you plan to bring to share

Hopefully we'll see the mountain laurel in full bloom but this is still a scenic hike with a terrific view from the top of Cobble Mountain, and there's a nice pond where we'll stop for a snack. The trail to Cobble has a short, challenging scramble but just about anyone can do it with some assistance. There's also an off-trail walk-around, but you'll be on your own for that.

Back at the pavilion, we'll fire up the large charcoal grill and get busy with some burgers and whatever else you brought to share. Afterward, a tug-o'-war challenge!

Lake George Weekend!

Needs a location

Three days and nights of hiking and revelry on and around the lake, including hikes up Buck Mountain and Crane Mountain, and a dinner cruise Saturday evening.

Come and go as you want and book a room wherever you like. I’ll be at America’s Best Value Inn & Suites Thursday, Friday and Saturday nights.

Once your room is booked, private message me and I’ll move you to the going list. Please keep the comment section clear for important messages, and frivolous shenanigans 🤪

If you’re booking the dinner cruise be sure to select the Lac du Saint Sacrement Sunset dinner cruise for Saturday, June 25, AND BE SURE TO CALL[masked] ex. 4 AND MENTION THE GROUP NAME TO ENSURE WE ALL SIT TOGETHER.

Did you get the part about mentioning the group name when reserving the cruise? Ok good 😆

The link below takes you to available cruises but you’ll have to scroll your way to the Lac du Saint Sacrement Sunset Dinner Cruise.


Tentative itinerary:


Early arrivals meet up for dinner and drinks around 7 PM


10 AM - Hike Buck Mountain. Please carpool from town as parking is very limited. Lunch and drinks at Adirondack Brewing Company (or elsewhere) after the hike, followed by drunk mini golf 🥴


10 AM - Hike Crane Mountain. We’ll meet in town at 9 and carpool to the trail. Lunch wherever.

6 PM - meet at Lake George Steamboat Co. to board 6:30 dinner cruise. Nightlife in town afterward.


On your own - hike, shop, play mini golf, hang out and enjoy the lake, depart


Buck Mountain hike - 4🍺 of 6 in difficulty, 7 miles up and back, 4+ hours, 2000 feet hellevation gain

Crane Mountain hike - 5🍺 of 6 in difficulty, 3 mile loop, 3.5 hours, 1400 feet hellevation gain. There’s some bouldering involved with this hike so it’s not suitable for everyone.

Several shorter hikes are accessible near Lake George if you’re not up to the listed hikes.

Autumn in Ashville!

Needs a location



  • Thomas Jefferson's Monticello Estate
  • Entire Blue Ridge Parkway during peak leaf season
  • Mount Mitchell - highest mountain east of the Mississippi
  • 4 nights in Ashville, North Carolina
  • Biltmore Estate and winery - Largest home in America
  • Brief hike with amazing views in Great Smoky Mountains N.P.
  • 17 mile downhill bicycle ride along the Virginia Creeper Trail


$1700 - $2000 plus meals. Number of participants and final hotel selections will determine exact cost. If you share a room, this trip realistically can be done for about $1200 plus meals.

Accommodations will be modest, private, and comfortable.


Day 1 - Saturday

I’ll leave Rhinebeck at 8 AM with a 12-passenger van and collect people at prearranged pick-up points south of Rhinebeck, then we’ll continue to Charlottesville VA and stay overnight.

Day 2 - Sunday

Tour Monticello, home of Thomas Jefferson, Founding Father and slave monger. Begin traveling along Blue Ridge Parkway, overnight in Roanoke VA

Day 3 - Monday

Continue along Blue Ridge Parkway, detour to Mt. Mitchell, arrive in Ashville

Day 4 - Tuesday

Relax and explore Ashville, or go hiking. Maybe both. Maybe something else.

Day 5 - Wednesday

Tour Biltmore Estate, gardens, and winery. Evening in Ashville

Day 6 - Thursday

Drive to the heart of Great Smoky Mountains National Park for an easy hike to Clingmans Dome and Mount Love along the Tennessee border. Return via the final segment of the Blue Ridge Parkway. Last evening in Ashville.

Day 7 - Friday

Depart Ashville for Damascus VA, rent bicycles and enjoy an easy 2-3 hour, mostly downhill ride along a scenic brook. Overnight in Roanoke VA

Day 8 - Saturday

Travel to New York and drop everyone off by 6 PM. Hopefully.


Photos (3,679)