Even when unfettered by the standard 48-hour limit, reluctant weekend traveler Ben Neihart could never really appreciate the joys of leaving town. But he learned—and no, he won't be seeing you Monday

I used to be suspicious of long summer weekends. I'd get invitations. I'd feel the drumbeat all around. Get away. Sail to Newport. Canoe to Maine. Escape. But why? I'd wonder. Lovely sunshine drenched my Brooklyn apartment; the park, with its tennis courts and picnickers, was right across the street. The days were so long and the air so sweet, even in my neighborhood. Fig trees bloomed in the backyard garden.

The long weekend as a tradition dates to 18th-century Europe. Skilled craftsmen and tradesmen, weavers and cobblers, found freedom by working longer hours in order to work fewer days. Over time, they began to take off "Saint Monday"—otherwise known as the Monday after payday. Yes, an astonishing amount of liquor was consumed. Mondays, soon enough, became boon days for attendance at horse races, boxing matches, museums, and concerts.

All evidence to the contrary, sometimes we Americans act as if we had invented the long weekend, but that's not hard to understand. Because of changes in the ways we work, study, and raise our families—flextime, the midlife medical degree, the exuberant grandparents who've moved to Costa Rica—we are accustomed to reshaping our weeks. The astonishing opportunities afforded by the airline and hotel industries make us feel like modern pioneers. We tend not to take the monthlong family holidays that our friends in other parts of the world do, so these variations on the weekend come naturally to us. We like to push our own limits, to ask ourselves just how much we can do regardless of the constraints of time.

We all have our best seasons, our favored travel rituals. I believe my peak time is the summer, and my vacation clock is best set to slow. When I took a long summer weekend, I'd never figure out the proper proportions—I'd end up with seven days' intentions busting the lining of my allotted 72 hours. I'm not a tragic hero, but during my misbegotten Memorial Day and Fourth of July weekends, I'd find myself behaving like the twitchy actor in what film critics call a "clock movie"—that is, one of those summer blockbusters in which the quick-ticking passage of time pits a man against a bomb, a verdict, a showdown in the town square. I have been told by those closest to me that I have actually pitched fits (in New Orleans, trapped on the wrong side of a parade route, desperate for a cab to Lilette; north of Copenhagen, wedding-bound, my backside nearly aflame from the car's seat-heater gone awry). But these tattletale friends, honestly, are prone to hyperbole.

I have had to train myself to enjoy weekend travel, but I'm not going to lie and say that my conditioning was a hardship. During the summer, when the days linger, when an abundance of federal holidays punctuate the months, I used to practice my long-weekending skills at weddings. The rituals, the rigid schedules, and the complicated wardrobe requirements frayed my nerves, but in the margins of the getaway I started to understand the appeal of what Bridget Jones called a mini-break.

A few years ago, I was a guest at the nuptials of a friend I'd worked with at an international relief agency. The celebration was in the Sonoma Valley, a traditional church ceremony followed by the multiple festivities that befitted the merging of Korean and Italian families. An hour after checking into the quaint hotel, one of my fellow travelers, Lynn, who was another of the many former colleagues in tow, totaled the car we were sharing as she backed out of the parking lot. We were going under 10 miles per hour. We had traveled less than three yards. We weren't hurt, we were insured, and the glorious Healdsburg sun still shone. Hotel acquaintances offered help; when they found out we were okay, they offered vineyard and restaurant tips. Poolside, we were able to arrange another rental in less than an hour. But suddenly, our perspective shifted. We'd lost a bit of time and a bit of money, we'd fallen off our schedule, and now, somehow, the vacation was ours. We had wonderful obligations, but this trip was not work, not three days to struggle through. Pulling into the J Winery parking lot, with its fairy-tale bridges and bubble machine, we joked that our "mild" concussions were causing hallucinations, that northern California was, materially, no prettier than midtown Manhattan. Then we agreed to banish home from our vocabulary till Sunday.

From weddings, I've graduated to other kinds of long summer weekends. I've gone, off-season, to Caribbean beach resorts I wouldn't have been able to afford in midwinter; in paradise, I learned, my inner clock slows by the end of the first day. Coming home from the Turks and Caicos on a Monday afternoon, I've found myself marveling at the light air traffic, the friendlier service. With some traveling chums, a long weekend may even be sweeter than a weeklong holiday; you love these vigorous pals, in the proper dose. And while I haven't yet tried it, each year I promise myself that I'll make a dash for Paris or Florence, an haute version of the road trips I used to love in college, four days and three nights, but with real beds. And air-conditioning.

For many, many years—aeons, actually—mankind lived season to season, hunting and gathering. Then, skipping ahead to about A.D. 300, the Romans invented the seven-day week. It was only a matter of time before the single day of rest swelled into a "weekend" and then spawned languorous additions—Mondays and Fridays (and even Thursdays). These are the highlights.
—Luke Barr

The term week-end is first used in the English magazine Notes and Queries. It was described as lasting a day and a half, since Saturday morning was still part of the workweek.

Labor Day becomes the first American holiday to be designated as a Monday, thereby yielding a long weekend. Congress makes the holiday—which was, not surprisingly, invented by a labor union—the law of the land.

Jay Gatsby throws lavish parties all summer at his West Egg spread in F. Scott Fitzgerald's novel, and Long Island's place in the firmament of classic long-weekend destinations is secured.

President Eisenhower inaugurates the Interstate Highway System as car culture takes off; families pack themselves into their station wagons for road trips to see relatives in Baltimore.

Boeing introduces the 707, bringing the coasts to within six hours of each other. Not long after, the jet set is heading to Barbados for the weekend.

With JFK's election, the Kennedy Compound in Hyannis Port becomes the unofficial summer White House and the site of many iconic, windswept weekend photographs, with and without footballs.

The observance of Memorial Day is established on a Monday. Summer now has a de facto starting point—a three-day weekend to kick things off.

The Big Chill gives the long weekend its definitive sound track.

Corporate "casual Fridays" proliferate. People come to work dressed for the weekend—and then leave early to get a head start.

Priceline.com begins auctioning off unsold airline tickets, creating a market for last-minute travelers in the process.

Scientists predict that by the year 2020, weekends will officially begin on Wednesdays at precisely 1:45. The French will have ceased working altogether.