Six cities, six historic arenas, two countries, and more than a century of tradition — the NHL Original Six road trip turns a run of regular-season games into one unforgettable journey. Seeing Montreal, Toronto, Boston, New York, Chicago, and Detroit on a single trip connects you to the clubs that carried the league through its early decades, and every stop brings its own rink culture, neighborhood, and travel rhythm. The reward is obvious; the real challenge is coordination, because six home schedules, several travel legs, and two border crossings all have to line up inside one tidy window. Below is how the route fits together, when to go, and how to keep the planning simple enough that you can focus on the hockey instead of a spreadsheet.

What Is the NHL Original Six Road Trip?

The Original Six are the franchises that made up the entire NHL during one of its most storied stretches. The Original Six era ran from the 1942-43 season through 1966-67, when the league was built around just six clubs: the Boston Bruins, Chicago Black Hawks, Detroit Red Wings, Montreal Canadiens, New York Rangers, and Toronto Maple Leafs, according to the league’s own history. Modern expansion has grown the NHL well beyond those teams, but the six originals still carry a weight and a rivalry history that newer franchises simply cannot replicate. A trip built around them traces the league’s roots from one founding city to the next.

Why Fans Make the Trip

A road trip that links all six in one itinerary is a bucket-list goal for dedicated hockey fans. You move from one passionate market to the next, comparing buildings, anthems, rivalries, and pregame neighborhoods along the way. One night you are surrounded by a bilingual crowd that treats the game like a civic event; a few days later you are in a midtown arena where the energy feels completely different. The contrast between stops is exactly what makes it memorable.

Which Cities and Arenas Are on the Route?

The trip covers six markets across the northeastern United States, the Midwest, and two Canadian cities. Each one pairs a famous arena with a downtown worth exploring, so the hours around each game matter almost as much as the game itself.

  • Montreal Canadiens — Bell Centre: Widely regarded as the spiritual home of the sport, with an atmosphere that builds quickly on rivalry nights and a crowd that treats hockey as part of the city’s identity. Pair the game with Montreal’s celebrated food scene and café-lined neighborhoods.
  • Toronto Maple Leafs — Scotiabank Arena: A marquee downtown stop in the heart of the financial district, ringed by restaurants and bars and steps from the waterfront and major transit.
  • Boston Bruins — TD Garden: A loud, knowledgeable crowd in an arena perched above a major transit hub, with the North End’s restaurants a short walk away. Few buildings deliver Original Six intensity quite like it on a rivalry night.
  • New York Rangers — Madison Square Garden: One of the most famous buildings in all of sports, set in the middle of Manhattan, where endless dining, shows, and nightlife make it easy to extend your visit.
  • Chicago Blackhawks — United Center: Home to a famously thunderous pregame anthem and a passionate fan base, with Chicago’s renowned food scene, museums, and lakefront only a short ride from the arena.
  • Detroit Red Wings — Little Caesars Arena: A modern arena anchoring a downtown entertainment district, surrounded by a dining, music, and culture scene that makes an easy final stop.

No two stops feel the same, which is the whole point. Visiting all six back to back shows just how distinct each market’s relationship with the game really is.

How Do You Route and Time the Trip?

Most travelers group the four eastern stops — Montreal, Toronto, Boston, and New York — and pair them with the two Midwest cities, Chicago and Detroit, at the start or the end of the trip. The eastern leg is compact enough that short flights and, in places, rail connect the cities without much hassle. A common approach starts in Montreal and works south and west, finishing in Chicago or Detroit. Plan on roughly seven to ten days, depending on how much non-hockey time you want in each city along the way.

Routing Options to Weigh

There is no single correct order, only the order the schedule allows. Some travelers clear both border crossings early by opening in Montreal and Toronto, then settle into the U.S. cities; others save Canada for the end. The two Midwest stops make flexible bookends — Chicago and Detroit sit close enough to pair naturally, whether you tackle them first and fly east or finish there. Whichever direction you choose, avoid backtracking: a route that keeps moving one way trims travel time and transfer costs and leaves more daylight for seeing each city.

A Sample Flow

  • Montreal: Open in hockey’s spiritual home, then continue to Toronto by road or a short flight.
  • Toronto: Catch a downtown game, explore the markets and waterfront, then head east toward Boston.
  • Boston: Take in a game and the surrounding neighborhoods before continuing south to New York.
  • New York: Build in an extra day if you can — the city rewards a longer stay — then fly to Chicago.
  • Chicago: Enjoy the anthem, the food, and the lakefront before the final hop over to Detroit.
  • Detroit: Close the trip downtown, then fly home from your last arena of the tour.

On timing, the home schedule is the constraint that shapes everything else. NHL schedules are released in the offseason, which gives you months to find a window where all six teams are home on or near the dates you need. Because each club plays at home on only part of its calendar, the densest stretches of home dates tend to fall in the heart of winter — a practical target for lining up all six games inside one week-and-a-half window. Build in a little slack, too, because a road back-to-back for even one team can force you to reshuffle the route.

How Do You Plan Six Cities Without the Stress?

The hard part of this trip is not any single city — it is making six schedules, six hotels, and several travel legs line up into one smooth, well-paced journey. A little structure up front keeps game days relaxed instead of rushed. The checklist below covers the decisions that matter most.

Planning Checklist

  • Start with the schedule: Once the season’s dates are released, map a seven-to-ten-day window where every team has a home game you can reach. Everything else follows from that alignment, so lock it in first.
  • Stay near each arena: Booking downtown, within reach of the building, simplifies game nights and lets you soak in the pregame neighborhood at each stop instead of fighting traffic.
  • Carry a passport: Montreal and Toronto are in Canada, so a valid passport is required for U.S. travelers crossing the border for those two stops. Confirm yours is current early.
  • Plan your transfers in advance: Short flights handle the long jumps, while rail and driving can cover some of the shorter eastern and Midwest legs. Decide each transfer ahead of time so travel days stay calm.
  • Consider one coordinated booking: Pulling tickets, hotels, and transfers together avoids juggling six separate purchases and reduces the chance that one missed connection unravels the rest of the trip.

The border crossings deserve special attention. Montreal and Toronto sit in Canada, so U.S. travelers need a valid passport, and depending on your route you may cross into and out of Canada more than once. Confirm every passport in your group is current with comfortable margin, and remember that renewals can take weeks. If you are driving across the border on game day, leave extra time for the crossing so a slow line never costs you the opening faceoff.

Where you sleep matters more than usual on a trip like this. A hotel within walking distance or a short ride of each arena turns game night into the easy part: you arrive early, enjoy the pregame neighborhood, and head back without a long late-night transfer. Coordinating six bookings around six arrival times across two countries is fiddly, which is one reason many fans hand the arena-area hotel piece to someone who arranges it routinely.

For many fans, the simplest path is to let a specialist handle the moving parts. Major League Vacations can bundle game tickets, hotels near each arena, and intercity travel into one plan, drawing on dedicated city pages like Boston Bruins travel options and New York Rangers game-day travel. A coordinated package also gives you one point of contact if a schedule shifts or a connection slips. If you want a feel for the in-arena experience first, our overview of what to expect at an NHL arena is a useful primer for first-time visitors.

Ready to turn the Original Six into one seamless trip? Explore our NHL travel packages or build a custom Original Six itinerary, and our team will coordinate tickets, arena-area hotels, and city-to-city travel around the home dates that fit your schedule.

Frequently Asked Questions

How long does the NHL Original Six road trip take?

Most itineraries run about seven to ten days. A tighter seven-day plan gives you one game per city with travel days in between, while a ten-day version leaves room to explore Montreal, New York, and Chicago. The biggest variable is finding a window when all six teams are home.

Do I need a passport for the Original Six road trip?

Yes. Montreal and Toronto are in Canada, so U.S. travelers need a valid passport to cross the border for those two stops. It is worth confirming your passport is current well before you finalize the dates, since renewals can take several weeks.

What is a good time of year to plan the trip?

Midwinter is a popular target because the schedule is dense and most clubs are playing frequent home dates. Since the full schedule is released in the offseason, you can map your window months in advance once you know when each team is home.

In what order should I visit the six cities?

A common approach groups the eastern cities — Montreal, Toronto, Boston, and New York — and pairs them with Chicago and Detroit at one end. Many fans start in Montreal and work south and west, but the home schedule ultimately decides the order that works best.

Can I travel between the cities without renting a car?

Often, yes. Short flights cover the longer jumps, and rail connects several of the eastern cities. Some legs, especially in the Midwest, can be driven, but much of the route works without a car.

Can Major League Vacations plan the whole trip?

Yes. The Original Six road trip is exactly the kind of multi-city itinerary our team coordinates — pulling game tickets, hotels near each arena, and intercity travel into one plan so you can focus on the games instead of the logistics.