As an investor, founder, CEO and business book author, I write about startups, design, how to build a good business, and I like to muse about culture in any form.

2020 Road Trip Summary, in brief

It’s time for me to climb new peaks, personally and professionally.

The day after I left Grommet, I called my close friend Anne Fahey and asked, “Are you up for a road trip in September?” Anne and I have known each other since age 17 and shared every point of our adult lives. It made sense to share this adventure too.

In fact, the only other major US road trip I ever took was with Anne. In 1981 we travelled from Ann Arbor to Chapel Hill–to drop off our pal Claudia at med school. It was time to get back on the open road!

I’ve always wanted to hike the Colorado Rockies, so that was a starting point.

Trip by the numbers:

  • 28 days (9/11-10-9)
  • 19 different beds
  • One plane, two rental cars, three boats, one Segway
  • 3,176 miles travelled and 90 hours behind the wheel
  • Longest gap between meals: 24 hours
  • 424 sanitizer wipes used
  • 163 or 185 miles walked–depending on whose fitness counter you believe
  • 37 oldie but goodie stories retold
  • 17 Grommets packed and used
  • 80 mph speed limit through much of CO, WY and SD (hard to slow down after enjoying that)

The route:

  • Denver
  • Colorado: Breckenridge, Vail, Steamboat Springs, Grand Lake, Estes Park, Boulder, Denver.  (Hiked 11 out of 12 days in Colorado.)
  • Wyoming: Laramie and Devil’s Tower
  • South Dakota: Black Hills/Custer State Park and Badlands/Scenic
  • Minnesota: Minneapolis
  • Wisconsin: Bayfield/Lake Superior/Fruit Loop Tour
  • Michigan: Munising/Upper Peninsula, Mackinaw City/Dark Sky Park, Midland, Ann Arbor
  • Ohio: Cleveland
  • New Jersey: Princeton
  • Massachusetts: Boston

The best sight: A mother moose and her calf in Grand Lake, CO

The best event: Buffalo Roundup in Custer State Park, South Dakota–always the last Friday in September

The best experience: cycling in the Badlands of South Dakota

Best hike: Sky Pond in Rocky Mountain National Park

My hiking buddy of 20 years Jill McMahon joined us for the first 11 days in Colorado

Best foliage: Aspens in Dillon, CO, maples of Midland, MI and Western Pennsylvania (en route to New Jersey)

Dillon, CO
With the afore-mentioned Claudia, at Dow Gardens in Midland, MI
Dow Gardens in Midland, MI

Best tourist site: Wyoming Territorial Prison

Butch Cassidy was incarcerated here
The prisoners made brooms. There is still production of same at the prison, albeit by a normal paid workforce.

Biggest tourist trap/disappointment: Wall Drug. We actually needed drugstore type stuff when we visited, but it was just a sea of gee-gaws and very little drug store product. But, hey, the bison burgers and doughnuts were good.

The best meal (went there twice): Bird and Jim in Estes Park (especially the Rocky Mountain Trout)

Peach and tomato caprese salad with fabulous cornbread in background.

The best (and only) happy hour meal: Uchi in Denver (mind blowing and affordable sushi)

Dessert at Uchi: jasmine tea cream with honey crumble, cilantro granita and pineapple.

The single best thing I ate: a heavenly biscuit at Circle View Ranch in Scenic, South Dakota I inhaled it too quickly to take a photo, but take my word for it. World class.

The ranch is high up on this mesa, next to the White River. It is in the middle of the family’s 2,800 working cattle ranch. The breakfasts are homemade.

Best Coffee: WonderState in Bayfield, WI

Best breakfast: Snooze in Denver (a flight of pancakes)

Pineapple Upside Down Cake, Sweet Potato, Blueberry Danish

The scariest night: Lake Ranch in Devil’s Tower (Hulett, Wyoming)

What I drew in my travel journal that night at Lake Ranch

The most surprising places:

  • George Floyd’s Minneapolis neighborhood—stable middle-class homes (I guess I expected a rougher place with hopped up cops looking for trouble)
  • Midland, Michigan–so many natural and cultural amenities
Standing on a viewing platform on the Whiting Forest Canopy Walk (a 40 feet high elevated walkway, the longest in the country) in Midland, MI

Best quirky shopping: vintage stuff in Laramie, WY (but I forgot about Matthew Sheppard when we were there…and would have had trouble enjoying myself if had remembered that tragedy.)

Vintage glass rolling pin filled with buttons, locally made flour sack towel, old tobacco can repurposed for scary Halloween candle holder

Best boutique shopping: Joanne’s Scandinavian in Bayfield, Wisconsin

File:Joanne's Scandinavian Store - panoramio.jpg - Wikimedia Commons

Best rural art: Metal signs at ranches in CO, WY and SD

Best Urban Art: This mural that went up within two days of RBG’s passing, in Denver’s RiCo neighborhood.

Most listened to podcast: Hacks on Tap

Most used apps:

  • Trail Finder
  • Hiking Project
  • Yelp
  • Trip Advisor
  • Spotify
  • Apple Podcasts
  • Dark Sky
  • Google Maps

Best handling of COVID protocols: State of Colorado, Southwest Airlines, and the chain hotels

Sticker on door/frame to prove no breech since cleaning

Worst handling of COVID protocols: State of South Dakota and State Game Lodge in Custer State Park, SD

If I took the photo from the other direction, you would see lots of “free” and unemcumbered faces

Most Trump lawn signs: South Dakota

Most Biden lawn signs: Michigan

Almost no lawn signs: Colorado

Crabbiest moment: checking into State Game Lodge (my TripAdvisor review here)

Most transcendent moment: exploring around Circle View Ranch in South Dakota, in the early morning

Best beds:

  • Holiday Inn Express in Munising, MI
  • The Ramble, Denver
The Ramble

Place I would most want to live: Boulder, CO (in fact, why does ANYONE ever move away from Colorado?)

Hiking just outside of Boulder, at dawn

Most used item I packed: Zamberlan boots (see above)

Never used item (yay!): waterproof pants (see above)

Most useful purchase of trip: Cat Crap

Souvenir I think I will most appreciate: Tiny little bison painting by Ron Holyfield

Favorite new accessory acquired: Stormy Kromer beanie

At Presque Isle Falls, Michigan

Product that saved our 90-hours-in-a-car butts–literally: Purple Seat Cushion. I shipped two of these to one of our Colorado hotels. Claudia told me about them when I complained about working on a hard kitchen chair. I now own four, of different styles.

Most active tourist board: South Dakota

Best tour assist: Black Hills Tour Company

With our guide Joel, who brought us good bikes, good tips and a COVID-friendly picnic lunch to navigate the Badlands

Place that has not discovered Marketing (in a good way): family run orchards/cider mills near Bayfield, WI.

I am pretty sure we watched the family members who own the orchard process the apples for shipping to a grocer down south.
Example: we just happened to trip on a giant Sears and Roebuck mail order barn from 1927 that was FULL of memorabilia at Hauser’s Superior View Farm. One tiny sign “advertised” its existence.

Best body of water: Lake Michigan

View of Lake Michigan from Mackinaw Bridge

Most surprisingly boring driving: Upper Peninsula, MI

Most surprisingly NOT boring driving: Eastern Wyoming, South Dakota and Western Pennsylvania

South Dakota. The views were wide and I never get tired of that (as opposed to the tunnel of trees in the U.P.)

Biggest miss: Not seeing the northern lights at the Headlands International Dark Sky Park in Mackinaw City, MI (good excuse to go to Norway or Hawaii.) They are notoriously elusive but we gave it a good college try for the two nights booked there.

Most frequent activity (apart from eating and hiking): Visiting botanical Gardens—in Vail, Denver, and Midland

Those are plants!

Best travelling buddies in 2020: Anne Fahey and Jill McMahon

Anne, Jill and I at Fern Lake, at Rocky Mountain National Park. A nice visitor from Florida unfortunately discovered it is a haven for leeches.

Next road trip for Anne and Jules: down south, starting with Montgomery, Alabama because of The National Memorial for Peace and Justice.

Black Hills, South Dakota
Steamboat Springs, CO. Coffee. Always coffee. Jill’s looking into a Norwegian adventure for us–on a boat that gets you into hard to reach places for hiking (or cross country skiing.)
Lake Michigan
Black Hills, South Dakota
Rocky Mountain National Park
Pontoon boat in Grand Lake, CO
Mount Rushmore

P.S. Our COVID-19 Precautions:

  • Masks at all times except in car, hotel rooms, while eating, or hiking on empty trails. About 60-70% of hikers deployed masks.
  • Eating outside the majority of the time. Indoor restaurants were generally well spaced with a minimum of contacts (like QR code menus). For some reason chairs freak me out a bit–they don’t clean them well enough.
  • Wiping down touch points in hotel rooms
  • Wiping down car after going in a business or hiking
  • Avoiding crowds, Buffalo Round Up excepted
  • Arranged a couple of private tours in SD with Black Hills Tours–for areas where we anticipated both a high number of sites to see, and large crowds
  • Sanitizing hands before, and after, going in a business. Some restaurants also took our temperatures, which we welcomed. Many stores required sanitizing before entering.
  • Even on a hike, sanitizing hands when scrambling and using our hands to grab a rock or branch other people might have grabbed
  • Anne also used gloves, a medical grade mask, and goggles on her flight. I just sanitized and used a mask, but no one was near me.
  • Got a rapid COVID test in Minneapolis (after seeing South Dakota) and then a PCR test the day after I got home to Boston (both negative)


21 Responses to “2020 Road Trip Summary, in brief”

  1. Grace Wilson

    So fun to read about your trip and follow through Instagram. Our trip was much shorter but we had a lot of overlap and I recognized a bunch of the same things. I’m in Telluride now and it’s a magical place. Lots of history and character from its mining roots. I’m jealous my brother gets to live here all winter. He can see the ski slopes from the desk he set up in his room. Below is a picture of his street. Great hiking here too! You and your friends should add this place to your list!

    • julespieri

      Thanks Grace…ahead of you on Telluride. Jill and I have hiked there because I have been a mentor at the Telluride Venture Accelerator. So I am jealous of your brother too!

  2. MaryAnne Gucciardi

    Thanks for sharing your adventure, Jules. I feasted on all the photos. Dreamy. My best to you and yours, MA

  3. ps8649

    Loved,  loved,  loved all of it — descriptions, photos, etc. And, of course, your hotel review.  Can’t believe they were still having a buffet. So glad you did much more than hike.😍

    • julespieri

      I know! It came just after our 24 hours with no food so we sadly had to partake. We’d had no dinner at Lake Ranch (the creepy place) and the Buffalo Roundup pancake breakfast ran out just as we got there… the hotel is in the park so they were the only game in town. With. A. Buffet. There were gloves but half the people did not use them. UGH.

  4. Sandrine Park

    What a wonderful recap! It was a joy to read. Thank you for sharing, Jules!

    Sent from my iPhone


  5. Nancy

    Love a good road trip, Jules, especially when it’s focused on natural beauty, adventure, and discovery. Next time you’re in CO head to Ft. Collins to experience our classmate Ginger’s “Ginger and Baker” pie shop/cafe/restaurant/event space/outdoor space.

  6. Cathy

    Spectacular Jules. You’re reminding me that driving cross country has been on my list for decades. With two high school seniors, maybe that should be my first empty nest project! Thank you so much for sharing and inspiring.

    • julespieri

      Highly recommend. I typically prefer a vacation that involves a rental home and more chilling out. But each of the days on this road trip stand out in a way that a more stationary holiday could not.

  7. Micah Chae

    What a wonderful post Jules. Thanks for the entertaining summary. Took a long bike ride after many years at my company. Loved the journey. Haven’t arrived at a new destination. Still loving the journey. Wishing you many many more.

  8. Matt Norton

    So cool Jules … really enjoyed it. Happy to help you and Anne plan an itinerary for doing the Wild Atlantic Way in Ireland if it’s of interest after Covid has allowed us (hopefully) to return to a more normal way of living ..


Leave a Reply to “Four H Club” Trip Down South | Jules Pieri Cancel reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Basic HTML is allowed. Your email address will not be published.

Subscribe to this comment feed via RSS

%d bloggers like this: