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The best places to ride retro vehicles in America

Where to ride American classic planes, trains, and cars

By Ella Buchan · October 13, 2025

Originally published on loveEXPLORING

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Vintage vehicles

It’s nice to gaze at beautiful classic cars, 1940s aircraft, and vintage train carriages in a museum or at a festival. But to truly experience these feats of engineering and aerodynamics, you need to take a ride in them.

Click through this gallery to see the best places around the US where you can be transported back in time with a journey in a retro vehicle...

AmericanDreamTourMiami/Facebook

American Dream Tour, Miami, Florida

There can’t be a more appropriate way to tour the most glamorous parts of Miami than in a top-down vintage car. American Dream Tour has a fleet of retro convertibles including a 1960 Buick Electra and a white-and-spearmint 1959 Edsel Corsair.

Guests take a back seat or ride shotgun as a chauffeur navigates the Art Deco streets near Miami Beach; or hip Wynwood, whose walls are plastered with bright street art.

AmericanDreamTourMiami/Facebook

American Dream Tour, Miami, Florida

You probably won’t want to get out at the end of the tour. Thankfully, you can also hire one of the gorgeous cars for big occasions, from weddings to family reunions – and pretend to be a 1950s movie star for a day.

OwlsHeadTransportationMuseum/Facebook

Owls Head Transportation Museum, Owls Head, Maine

You could spend hours wandering around the displays of old-school motorbikes, bicycles, and cars at this charming museum, whose highlights include a 1907 Cadillac and a wooden-bodied Ford Station Wagon.

OwlsHeadTransportationMuseum/Facebook

Owls Head Transportation Museum, Owls Head, Maine

For the chance to really get hands-on though, visit during one of the many events and annual festivals, which include airshows and motor rallies.

SkunkTrain/Facebook

Skunk Train, Fort Bragg, California

The smelly-sounding Skunk Train is actually a delight, chugging through groves of ancient redwood trees, darting into tunnels, and crossing bridges to reach the granite cliffs and pools of Noyo River Canyon.

Located several hours north of San Francisco on the northern California coast, the 1925 train cars are propelled by a diesel-electric engine and a steam engine.

SkunkTrain/Facebook

Skunk Train, Fort Bragg, California

The Fort Bragg Railroad was formed in 1885 to transport workers and lumber between logging camps, while the nickname "Skunk" refers to the pungent fumes the first gasoline-powered railcars released.

Now you’re more likely to sniff the scents of the forest or, if you’re on the popular Magical Christmas Train, hot chocolate and cookies.

Commemorative Air Force B29 B24 Squadron/Facebook

CAF AirPower History Tour, various locations

Always fancied piloting an aircraft? This ongoing tour, organized by the Commemorative Air Force, takes restored and airworthy military planes to locations across the US.

OK, so you won’t actually be able to take the controls, but you can take a spin in rare planes such as World War II bomber B-29 Superfortress, nicknamed "FIFI."

Commemorative Air Force B29 B24 Squadron/Facebook

CAF AirPower History Tour, various locations

The most coveted seat – and the best way to feel like you’re actually flying this thing – is the bombardier, in front of the pilots and with incredible views. Just be sure to choose your wingman or woman wisely.

ThompsonSpeedway/Facebook

Thompson Speedway Motorsports Park, Thompson, Connecticut

These are classic cars of a different (and perhaps less refined) kind. Think speed, guts, and glory rather than country lanes, plush leather seats, and huge steering wheels.

This motorsports park hosts NASCAR races and also allows amateur drivers to have a go on the 1.7-mile circuit.

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ThompsonSpeedway/Facebook

Thompson Speedway Motorsports Park, Thompson, Connecticut

Bookable experiences include racing in a powerful American muscle car or taking a one-day course in track driving – including plenty of time behind the wheel.

There are also regular vintage car and motorcycle festivals here.

PearlHarborWarbirds/Instagram

Pearl Harbor Warbirds, Oahu, Hawaii

Passengers are flown back to 1941 on this immersive tour, even donning World War II-style flight gear and undergoing pre-flight training before hopping aboard.

The bright yellow and red T-6 trainer plane, dubbed the "Pilot Maker," follows routes taken by military air personnel following the infamous bombing.

PearlHarborWarbirds/Facebook

Pearl Harbor Warbirds, Oahu, Hawaii

Two options are available: the affordable Ensign’s Warbird Experience, which will see you flying basic maneuvers around Kalaeloa Airport.

There's also the longer Admiral’s Warbird Adventure, which follows the flight routes used by the Japanese attackers.

Kenneth Sponsler/Shutterstock

Cuyahoga Valley Scenic Railroad, Peninsula, Ohio

This heritage railroad has 26 miles of track weaving through vast Cuyahoga Valley National Park, tracing the route of the Cuyahoga River and passing through the dense forest habitats of eagles and deer.

The fleet includes several 1940s sleeper and observation cars from the legendary California Zephyr, known as "the Silver Lady."

Kevin Vance/Flickr/CC BY-ND 2.0

Cuyahoga Valley Scenic Railroad, Peninsula, Ohio

Visitors can board at any of three main stations for a scenic ride. And the views will look even better combined with a drink or something to eat.

The company offers breakfast and dinner rides, plus a range of themed journeys and events including wine tasting, night bingo, and a murder mystery. 

ClassicCarsLasVegas/Facebook

Classic & Collectible Cars, Las Vegas, Nevada

Where better to pose behind the wheel of a classic convertible than along the Las Vegas Strip? This company specializes in rare and vintage vehicles, many of which are loaned for filming and commercial displays.

ClassicCarsLasVegas/Facebook

Classic & Collectible Cars, Las Vega

But they also have a few gorgeous numbers available for individuals to rent for a 24-hour period, including a red 1968 Mustang or silver-blue 1961 Cadillac Series 62 Convertible. Just don’t scratch the paint.

WineTrain/Facebook

Napa Valley Wine Train, St Helena, California

You can mix the grape and the train with this Napa Valley classic – one of the most leisurely ways to explore the area’s celebrated wineries.

The Wine Train runs on a 36-mile loop from Downtown Napa to charming St Helena and offers a range of packages, from lavish onboard lunches to a full day visiting vineyards for tours and tastings.

WineTrain/Facebook

Napa Valley Wine Train, St Helena, California

It isn’t just about the wine, though. There’s a lot of history packed into these century-old rail cars, which trundle elegantly along a route stretching back more than 150 years.

The carriages, with opulent velvet-upholstered seats, mahogany paneling, and brass, have been sensitively restored to evoke the glamor of vintage train travel.

WIGNRR/Facebook

Wisconsin Great Northern Railroad, Trego, Wisconsin

In Wisconsin, passengers can spend the night onboard a restored locomotive, which runs on track laid more than 100 years ago, tracing the Namekagon River in the picturesque St Croix National Park System.

WIGNRR/Facebook

Wisconsin Great Northern Railroad, Trego, Wisconsin

A dinner, bed (there are rooms on board) and breakfast package is one of many ways to experience the route. Another is the Family Pizza Trail – riders get half a pizza and soft drinks on the 90-minute ride.

BayAviationOnline/Facebook

Bay Aviation, Topping, Virginia

The cute, colorful aircraft at Bay Aviation look pretty spectacular from the ground. The view’s even better from the cockpit, though, as the planes are kept in an enviable location in Middlesex County on Virginia's Middle Peninsula.

BayAviationOnline/Facebook

Bay Aviation, Topping, Virginia

Skim over the broad, blue Rappahannock and Piankatank rivers in a 1943 PT-19 – one of fewer than 100 fully airworthy examples of the aircraft left – or take a scenic cruise in a Cessna 172 Skyhawk.

The cockpit is open, so you'll really feel the wind in your hair.

VerdeCanyonRail/Facebook

Verde Canyon Railroad, Clarkdale, Arizona

It’s hard to know where to look when you’re on board this vintage train, pulled by FP7 locomotives dating from 1953. There are the carriages themselves, with plush, comfy seats and retro décor. There’s the drinks menu or, if you’re in first class, your complimentary glass of Champagne.

But, once the journey gets underway, your eyes will probably be fixed on what’s going on outside.

VerdeCanyonRail/Facebook

Verde Canyon Railroad, Clarkdale, Arizona

The 40-mile round trip takes passengers through the dramatically beautiful Verde Canyon, skimming past craggy red rock buttes and the teal-hued Verde River. There are some pretty luxurious options on board, such as the caboose carriage for private groups.

There's one ticket, however, that trumps even swivel armchairs and complimentary Champagne: the locomotive ride-along, where one person each day gets to ride in the cab.

LumberjackSteamTrain/Facebook

The Lumberjack Train, Laona, Wisconsin

Journeys on the Camp 5 Museum’s vintage steam locomotive, built in 1916, follow a route taken in the late 1800s when the line served logging camps.

Passengers can sit in an original caboose or watch the scenery from an open-air observation car en route to an original logging camp and museum in the forest.

LumberjackSteamTrain/Facebook

The Lumberjack Train, Laona, Wisconsin

The Lumberjack Steam Train also hosts special events throughout the year, including an authentic cowboy reenactment and robbery of the train (pictured) – while you’re on it!

Keep an eye on the Lumberjack Steam Train website for details. Also note that the reenactment will add another $2 to your ticket price.

Laura Jackson/loveEXPLORING

Military Aviation Museum, Virginia Beach, Virginia

Virginia Beach might be known for its trio of glorious sandy stretches and outstanding oysters but it's also where you'll find the Military Aviation Museum, one of the world's largest privately-owned collections of World War I and II aircraft.

There are several large hangars at this family-friendly museum, all packed with planes including the P-51 Mustang pictured here. And thanks to the love and care given to the aircraft by passionate museum staff, many can still take to the skies. 

Military Aviation Museum/Facebook

Military Aviation Museum, Virginia Beach, Virginia

In addition to regular air shows and summer camps, the museum offers private flights with a highly experienced pilot. One of the most popular is a trip in the 1941 Boeing Stearman.

You'll soar over Virginia Beach, the Intracoastal Waterway, and head south of the museum to see the Back Bay Wildlife Refuge too.

OfficialCAFSoCal/Facebook

CAF Southern California Wing, Camarillo, California

Tucked into tiny Camarillo Airport, around 60 miles west of LA, southern California’s wing of the Commemorative Air Force (CAF) has a fascinating museum filled with aircraft and related artifacts from World War II. And these warbirds can fly too.

OfficialCAFSoCal/Facebook

CAF Southern California Wing, Camarillo, California

The museum’s Warbird Ride Program offers the chance to fly in aircraft including a vintage US Navy bomber and the PT-19, whose open-air cockpit will turn even the straightest, tamest hair into a bouffant.

Rides are scheduled most weekends and cruise over the creamy beaches of the surf city, Ventura.

Nowaday Vintage Car Tours

Nowaday Vintage Car Tours, New York City, New York

Revving up its engines since 2019, this vintage car cruise on the streets of New York is easily the best way to travel back to 1920s NYC.

Your chauffeur-turned-guide talks you through the city's fascinating history, including the Prohibition Era, the Jazz Age, and the Great Depression, as you sit on the plush leather seats of a fully restored Hudson Great 8 or Ford Model A.

Nowaday Vintage Car Tours

Nowaday Vintage Car Tours, New York City, New York

Take your pick of fun-filled rides around the Big Apple, from night-time drives in the City That Never Sleeps, to a speakeasy-themed tour you'll never forget.

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Now discover North America's most amazing rail journeys

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