How can you put a price on freedom?

Unforgettably charming and authentic road trip with a posse of interesting fellow enthusiasts on the most beautiful roads in this part of the world – priceless! Poetry and Visa commercial satire aside, the regular entry fee is $4999 (per team, double occupancy), and the closing date for all entries is March 1st, 2019. Payment must be made in full, either by credit card, PayPal, or by check at the time of submission.

N.B. There are no refunds after June 1st, for any reason. If you're in for a penny, you're in for a pound.

What's included - am I getting my money's worth?

Two tickets... to paradise! Ha. We guarantee you'll have a once-in-lifetime experience – how can you put a price on that? Seriously, just about everything is included except gasoline: Two tickets to the Welcome BBQ. 4 days, 3 nights of unparalleled fun and adventure, including 3 first-class meals per day, and 3 four-star hotel nights. Track Day at Canaan Motor Club. Mt. Equinox hillclimb. And a couple of wicked cool challenges thrown in every day.

We will also be providing each team with an enviable 'swag bag' full of unique and practical old's cool clobber including a one-of-a-kind OCT automobile jersey, custom stickers and patches as well as a bunch of old school, genius accouterments and loot.

What's actually on the menu?

Delicious, interesting, top-drawer fun. The OCT will be a 4-day event, starting this year at Old's Cool Tour Headquarters in Weston, CT. Each day will be divided into stages, roughly as follows, subject to change.

Wednesday, September 4th, 2019. Arrival and Welcome BBQ. We have reserved rooms at the Delamar Southport, about a 15-minute drive away for those coming into town (not included in the entry fee). Cars and support vehicles will be parked at OCT HQ for the duration of the rally. Welcome BBQ will be from 5-9 pm at the Delamar. We will have tech inspection for all cars and any last-minute adjustments made on the spot. We'll invite some of the local collectors to bring their vehicles for an impromptu car show, and we'll also have a band filling the summer air with good vibrations. Transportation to the hotel will be available.

Thursday, September 5th, 2019. Pre-rally breakfast at the Delamar. Driver's/safety meeting at 7 am. Start time is 7:22, in honor of Sir Stirling Moss's start time/famous Mille Miglia Mercedes number. Cheeky reference; real start time is 7:30 am.

Day 1, Stage 1. OCT HQ - Yale, approximately 1 hour. Checkpoint at Yale is United Church on the Green. Stage 2. Yale - Brown, approximately 2 hours. Lunch at The Hope Club. Stage 3. Brown - Harvard, approximately 1 hour. Checkpoint is Harvard Yard (of 'pahk the cah in' fame). Stage 4. Harvard - Dartmouth, approximately 3 hours. Finish of Day 1 is on The Green at Dartmouth. We will have dinner, and have invited some old's cool car friends to join us, at The Hanover Inn.

Friday, September 6th, 2019. Breakfast at The Hanover Inn. Day 2, Stage 1: Canaan Raceway for a couple of timed laps. Stage 2: Canaan - Mt. Equinox (for a hillclimb and lunch with a view), approximately 3 hours. Stage 3: Mt. Equinox - Hemmings, approximately 1 hour. Pit stop and museum tour. Stage 4: Hemmings – Cornell, approximately 4 hours. Finish of Day 2 is with dinner and second overnight stop at The Statler Hotel.

Saturday, September 7th, 2019. Breakfast, The Statler Hotel. Day 3, Stage 1: Cornell – SCCA Autocross. Stage 2: SCCA – Lazy Brook Park for lunch. Stage 3: Lazy Brook Park - U. Penn, approximately 3 hours. Formal gala at Radnor Hunt Club and third overnight stop at The Inn at Penn Hotel.

Sunday, September 8th, 2019. Breakfast at The Inn at Penn Hotel. Day 4, Stage 1: U. Penn – Radnor Concours. Stage 2: Radnor - Princeton, approximately 2 hours. Lunch at The Cannon Club. Stage 3: Princeton - Columbia, approximately 2 1/2 hours. Checkpoint at Columbia is Daniel Chester French sculpture at The Low Library. Stage 4: Columbia - OCT HQ, approximately 1 1/2 hours. OCT HQ: Awards ceremony and farewell. Overnight at the Delamar for any hangers-on.

Who can enter?

The OCT was created with adventurous car enthusiasts in mind, young and old, as well as anyone interested in a smart-aleck, eclectic experience. Since there is also a broad mix out there of serious gear heads who have unique automobiles but who aren't Ivy Leaguers, literally or figuratively (ourselves included), they're more than welcome too. We'll include a few bikers too, just to break the mold. Each team (consisting of a driver and navigator, both of whom must be 18+ years old) will be able to compete as representatives of their school, or simply for the personal fame and glory of winning the Oneupmanship Cup, which will be given to the team with the highest overall score. The only hard-and-fast rule is that the cars must be as old as your graduation year, or 25 minimum.

Is this a race?

Absolutely not. The Old's Cool Tour is a GTA (Game-Tour-Adventure) event which means it's a casual, fun driving experience. All speed limits and traffic laws must be obeyed. There will, however, be points awarded (or subtracted) for the challenges outlined in the 'road book' – such as solving a Rubik's Cube, or rotating your car's tires by a certain milestone. We'll also compete on 2 timed laps at Canaan Motor Club, and are hoping to have a timed autocross course, both of which will be added to the overall score. We will also be doing the Mt. Equinox Hillclimb, and this will also have a competitive element to it. Side wagers, although officially frowned upon, are welcome.

Uncle Joe, far left, at Seekonk Speedway with Freddy Astle and driver Gene Le Tourneau, circa 1952.

There won't be any participation trophies, but the team with the highest overall score as determined by the judges will be awarded the 'Oneupmanship Cup'. There will also be the 'Uncle Joe' award for the craziest/coolest ham-and-egger (who actually finishes), with most or all of his faculties, and car, intact. Named after Joseph J. O'Connell, one of the best and funniest car and boat lover guys we've ever known. There's also the Mary Karl Award for smoothest and coolest overall participant.

What makes the Old's Cool Tour so special?

We think there's no better place to enjoy a vintage, wind-in-your-hair drive than New England in the late summer. The Ivy League schools are destinations, metaphorically for most of us, that give our tour depth and character. And style, too. School spirit and pride, Ivy or not, are important elements, and add a level of friendly competition that every other rally in the world we know of doesn't have. In fact, there will be several teams competing for their universities this year.

We are also trying to give OCT cheeky and original twists – this isn't just a la-di-da afternoon with a bunch of rich jerks in expensive, show-offy Ferraris on a pretty country or scenic mountain road (and then back in the garage before it rains) but a delicate weave in and out of fairly dense metropolitan areas and ideas – that'll make this particular jaunt fantastic, frustrating fun, and not necessarily well-suited for the faint of heart. We also want to have perpetual and slightly sophomoric game of sidebar oneupmanship going on with unexpected trivia(l) questions to answer, impromptu physical as well as mental challenges to conquer, and even riddles and equations that'll need to be solved.

Finally, we've loved Ivy League style our whole life, and have tried to live it in a go-to-hell way. We'd like OCT to represent and incarnate that sartorial excellence, and bring a Prep Unit vibe to a younger crowd with some wit and finesse. Doesn't mean we'll succeed, but we'll give it the old college try.

The real question is: Are you ready to go back to school?

Do I need to bring my own car?

No, we have several rally cars available for anyone who wants to come along for the ride but doesn't actually have a ride. You can also ship your car – we have several car transport options for you, if that's what you'd like to do. If you really want to be old school, you can drive your car here, rally with us, and then drive it home.

Can I fly solo?

Sure, if you want to. Most everyone will come with their compagne de voyage – wife or brother or buddy – the someone special they want to share this with. If you can't find a co-driver and want one, we'd be happy to pair you up.

Is there a dress code?

Yes, as per 'Chadwick'. Kidding! Of course there isn't a dress code per se, but we always like to class the place up, sartorially speaking, wherever we go. It is an 'Ivy-League' tour after all, so let's represent and dress comme il faut, Ladies and Gentlemen. The only kind of hard-and-fast rule is to never wear socks. Kidding. Do we even need to remind you that there'll be no nudity, of course. Nor even partial nakedness. But we would like to mention to you that there will be a 'spirit award' and we have seen some excellent vintage ensembles as well as some very creative juvenile hilarity in the past.

What about baggage?

If you're speaking figuratively, leave the psychodrama at home! Seriously, you can definitely bring as much luggage as you want – we will transport it to each overnight stop for you.

What do I really need to bring?

All of your paperwork needs to be in order before you can enter the OCT: driver's license, registration, insurance. We have a liability waiver with lots of fine print that you'll need to sign, as well as an emergency contact information form. Your car will also have to pass the tech inspection to be eligible for the rally.

We have several recommendations to make your rally experience more enjoyable (as well as your life in general), which we'll bullet-point here for your convenience. Obviously, we're not going to tell you how many pairs of socks to pack; if you don't know that, please stop reading now and continue playing Mine Craft in your mother's basement.

1. Sense of humor. This is the one, indispensable EDC item that should be at the top of everyone's list and close at hand, no matter who you are, or where you're going. It will give you a sense of perspective, common sense, and a whole Swiss Army Knife of other sanity savers and psyche salves that we won't go into here. Needless to say, keep it in your pocket, at the ready. There will be a spot quiz – faites attention.

2. "Be here now." I saw this sign (featuring a cell phone with a DO NOT slash through it) at the cash register of Mocha Motts in Vineyard Haven this past summer, and I think about it often. It didn't say get off your phone – which would have been to simplistic and banal – but went profound. So, if you are going to come on OCT, make sure you come.

3. A basic car repair/survival kit: ours includes: Vise Grips, duck tape, work gloves, headlamp, WD-40, paracord, tow rope, jumper cables, hammer, 10W-30, spray start, super glue, adjustable wrench, various bolts, hose clamps, and bits and bobs. We have our car manual with us at all times. We also pack a blanket (crocheted by Nana years ago), a fire extinguisher, canteen with cup, Primus stove, and a first-aid kit with Advil, Tylenol, DayQuil and Tums. We also have bottled water, energy bars and a can of Spam.

4. Ear plugs and ear buds. We carry ear plugs with us at all times: if we're at the racetrack for example, or a concert, or out hunting. If we want to take an impromptu nap or if the hotel is noisy – we really can't sleep without them now. We also don't go anywhere ever without ear buds – we can listen to music, talk on the phone, or watch a movie without bothering anyone else.

5. Baby wipes. We discovered them when the kids were in diapers, and we find them indispensable.

6. Chargers for all your electronic devices. Actually, bring two of each. And a spare.

7. One Up! This is our very own wicked/smart word game. It's easy (and hard) to play – it's kind of like Scrabble but way faster and funner. A quick, brainy break whenever needed is in the can.

8. A book. No matter the pace of today's world, and the plethora of gadgets and entertainment opportunities, we sometimes just like to retreat back into a good book. We carry two with us just in case:The 7 Habits of Highly Effective People by Stephen Covey, and West with the Night by Beryl Markham.

9. Atlas, or map(s) of the area. We also carry a compass.

10. An old's cool friend wears 'dog tags' around his neck, with his name, address, and phone number, which he also has his kids wear whenever they're traveling. He also has a P-38 "John Wayne" and small signal mirror strung on it too.

How can I sponsor the OCT?

The Old's Cool Tour will have several levels of sponsorship, which we'd like to think are more like partnerships – all of us working together to promote our mutual love (and driving) of vintage cars. Oneupmanship is already on board again this year as the Trophy Sponsor, and will be providing all the cool car clobber.

What we're really interested in is engagement, interaction, and inspiring a new generation more than anything. Instead of placing your logo on our website for a fee, which is completely unoriginal and boring, we'd much rather have you 'sponsor' a team from the local technical college who will buy a vintage car, for example, fix it up, and run it in the tour. We can auction it off at the end, or just give it to one of the worthy participants. A vintage breast-cancer awareness car fixed up and driven by a team of young women to show there are no gender lines when it comes to elbow grease. An underprivileged youth team without resources but with drive and vision. These types of hands-on participation will hopefully instill in the young people involved a love of the hobby, and a can-do and self-reliant attitude towards life that will give them the confidence and courage to succeed in anything they do.

Good old-fashioned sunshine-on-the-face fun in a red Alfa "Graduate".

We'd also like to have other industries and individuals who see the benefits of the old-school values we're trying to inspire in others by living them ourselves come on board. Let's get that start-up company making electric motorcycles to buy an old VW Beetle and install one of their engines in it for the ultimate repurpose-recycle-reuse project. Or, how about a chemical company (or chinese restaurant?) inviting a local high school team to convert a vintage Mercedes diesel to run on bio-fuel? Let's cast a broad, creative net with our universal old's cool theme and authenticity, rather than just limit ourselves to cars and colleges.

We'd love to hear how you and your organization could bring something excellent, original and exciting to the table.

Yes, I want to be part of this exciting journey >

Is there a charitable aspect to OCT?

We believe that capitalism, despite its numerous flaws, is still the best system ever invented to unleash human potential and bring the greatest good to the greatest number. Don't just take our word for it — read a few pages of de Tocqueville, or listen to Bono* if you don't believe us. Any Cuban on any street corner in Havana will sadly but wholeheartedly agree, too.

*Rock star preaches capitalism at Georgetown University: "Commerce (and) entrepreneurial capitalism take more people out of poverty than aid."

With this in mind, we've put together what we're calling "Old's Cool U." – a classical liberal education in a portable aluminum suitcase that contains the 10 greatest books in the history of mankind, with an 11th thrown in for all the Spinal Tappers out there. We believe that almost all of the knoweledge and wisdom you need to know to succeed in life is contained in these ten tombes. Teach a man to fish, metaphorically speaking, and he's confident, self-reliant and generous forever. We will be happy to donate one (or more) of these to the charity of your choice.

The Wyakin Warrior Foundation, based in Boise, Idaho, which helps severely wounded veterans to achieve business success and was founded by our good friend Jeff Bacon, will be one of the official charities of the OCT. Again, we'd like to encourage each charity to purchase, restore, and rally a vintage vehicle – elbow grease and sweat equity are the best investments in human capital you could ever make in our opinion – hard work and personal fulfillment are the most dignified way to get people back on their feet, hands down. We are working with WW to make this happen.

If you have another fund or foundation you'd like to recommend, please let us know. We aren't judgemental or prejudiced – how about a pink breast cancer car with an all-female crew? We know a lot of women who like to wrench and drive and compete, and do all of the above with gusto and style.

There's a lot of life lessons to be learned scattered about.

What's the bottom line?

We like to attack each day with courage and integrity. Wit, and a sense of fun wonder and possibilities too. If that sounds like you, then come aboard our naive and quixotic adventure. You can sign up here to receive more information or ask a question we haven't just answered:

If you have questions, give Johnny a call directly on 203.451.5127 and he'll make sure to reserve a spot for you. Happen to be in the area? Pop by the OCT HQ, located at 13 Wilson Road, Weston, Connecticut 06883 – door's always open.