11 Fun Ideas for Road Trip Holidays
No matter the time of year, road trips are always a fun way to explore new areas of the country and see tons of sights in one trip. A holiday-themed road trip provides even more opportunities to experience everything America has to offer, from special New Years' celebrations to Halloween festivals.
There are so many destinations in the U.S. with special celebrations throughout the year. It’s hard to choose where to go when different areas of the country all seem to have the best celebrations for different holidays. Read on to learn about some unique stops to consider on your next holiday road trip.
New Year's Eve is celebrated across the globe in some of the most fashionable ways. Although New York, New York is famous for its Times Square celebration, the weather, the crowds, and prices aren’t ideal for a road tripper looking to enjoy their holiday.
Instead, consider sunny Sarasota, Florida, where you can enjoy ringing in the new year without fighting the chilly city traffic. With outdoor dining, live music, and a block party with rides, games, and prizes, you’ll love counting down to the new year with the beach just a block away. The best part about traveling to Sarasota for New Year's Eve is that you’ll get to watch the Pineapple drop in the middle of downtown!
The most romantic day of the year always calls for chocolates and flowers… but don’t forget the wine! Head out West for Valentine’s Day to celebrate love in wine country. Take the scenic route through Napa Valley for a romantic drive through winding back roads.
Known for producing some of the best wine in the world, nothing is more romantic than taking a tour through the vineyards and doing a wine tasting with your partner. Book a couple’s package at a quaint B&B, and spend all weekend exploring the romance and beauty Napa Valley has to offer.
Although it may seem obvious, if you plan to make a road trip for Mardi Gras, the only destination you should have in mind is New Orleans. The French Quarter is known for its wild parades, colorful costumes, and a party that never ends. NOLA has historic bars and hotels that will keep the good times rolling the entire time you’re in town.
However, if you’re looking for something more low-key, check out the local spots just a few blocks up on Frenchmen Street. You’ll find great music ranging from jazz and blues to reggae and rock — not to mention amazing authentic food and culture that’s a bit more family-friendly.
St. Patrick’s Day
Make your way to the midwest in Chicago to celebrate St. Patty’s Day in style! The moment you step into the city you’ll notice Chicago takes this holiday very seriously. Start your day at one of the many Irish parades to get you in the spirit. From there, book a boat ride down the famously green-dyed Chicago River while sipping on green-dyed beer to feel lucky all day.
Later in the day, you can head over to the many restaurants and bars that will all be serving traditional corned beef and cabbage and wash it down with some Guinness. You may not find the end of the rainbow, but you’ll certainly feel like you found a pot of gold when celebrating this holiday in Chicago.
Cinco de Mayo
Fiesta for Cinco de Mayo in Old Town San Diego! This charming Southern California neighborhood hosts an annual Cinco de Mayo celebration featuring live music, car shows, and an Artisan Mercado displaying handmade arts and crafts from local Mexican artists.
The vibrant booths, live music, and dancing set the mood for a great party in the streets. Tons of restaurants participate in the event, which means the hardest decision you’ll have to make that day is which delicious spot you’ll want to try next.
There is no better place to celebrate Memorial Day than taking a trip to Washington D.C. The annual Memorial Day Parade down Constitution Avenue is fun for everyone and a great way to kick off the weekend. Live music and performances throughout the day at different locations in the city will keep you entertained.
Everywhere you turn in D.C. has historical significance, which makes celebrating this honored holiday even more special. Visit the National Mall memorials and walk through Arlington National Cemetary in remembrance of all those who have fought for freedom in America throughout the decades.
There’s almost nothing more American than baseball, so if you’re celebrating Memorial Day weekend in D.C. a great activity to add to your itinerary is to catch a Nationals game at Nationals Park. After the game, you’ll have plenty of beer gardens in the area to hopefully celebrate a Nationals win!
Hot dogs, fireworks, and country music. What more could you ask for on the Fourth of July? If you decide to road trip down to Nashville, Tennessee you will not find yourself missing out on any of the celebrations.
Nashville is already one of the top places to visit in the US — but for the Fourth of July weekend, it is the only place to be! Country stars drive into the city for weekend-long concerts and all of the honky tonks on Broadway will keep you busy all weekend. Enjoy some hot chicken and fireworks to wrap up the day and celebrate America in style.
Labor Day weekend is often the “last hoorah” of the summer, and what better way to wrap up the sunny season than at Bethany Beach, Delaware! Up and down the boardwalk you’ll find ice cream, salt water taffy, and the best french fries doused with malt vinegar.
Spend the entire day soaking up the last of summer’s rays at the beach, then head back to your rented cottage to wash the sand off and get ready for dinner. Whether you decide to dine at a fancy seafood restaurant or hop around at the beach dive bars, be sure to try at least one Orange Crush at the bar.
Jack O’lanterns, light displays, and pumpkins set the stage for an atmospheric Halloween in Sleepy Hollow, New York. This historic town where the Headless Horseman roams has all of the staple Halloween activities. From haunted hayrides and Gothic mansion tours to the tamer farmers market, live music, and street fairs, there’s something for everyone to have a spooky good time!
Make sure you pack your costume and sign up to participate in the Halloween 5k, then go trick-or-treating on All Hallows Eve. In addition to all this fun, Sleepy Hollow also puts their annual Great Jack O’Lantern Blaze where thousands of jack o’lanterns are lit and Halloween music is played for an immersive Halloween experience!
Colonial Williamsburg, Virginia Williamsburg is the perfect backdrop to your next Thanksgiving trip. Take tours of the historic buildings, shop colonial goods and toys, or take a whimsical carriage ride around the town and take yourself back to the time when America was just getting its start.
Book yourself an authentic candle-lit Thanksgiving dinner where even the servers are dressed in historical garb. Surrounding yourself with the memories of one of America’s earliest colonial towns will not only be a great time but will also bring a new meaning to Thanksgiving.
They say there’s no place like home for Christmas. Once you’ve spent a holiday in Vail, Colorado, you may disagree.
Whether you’re a novice skier or feel comfortable gliding down the black diamonds, Vail provides the quintessential mountain town backdrop to your picture-perfect holiday trip. Decked out in Christmas trees and lights, offering cozy cabins to rent for the week, the only thing you’ll need to worry about is if Santa will be able to find you on Christmas Eve.
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