13 top Presidents’ Day weekend getaway ideas

The holiday season may be over, but that doesn’t mean the winter fun has to end. With Presidents’ Day weekend coming up, you’ve got the perfect excuse to get out and explore. The USA’s varied cityscape is optimal for romantic getaways, family-friendly adventures, and memorable trips with friends. 

When is Presidents’ Day? Officially, the holiday is celebrated on the third Monday in February, or February 19, 2024. It’s the last long weekend in winter and a good time to have an adventure in a new city. Plus, you can avoid the holiday’s increased air travel by renting a 15-passenger van with your favorite companions and hitting the road instead. 

The team of experts at Greenvans is here to help you plan the ultimate Presidents’ Day weekend getaway to any of the 13 road trip destinations below. 

1. Philadelphia, PA

Is there a better place to celebrate Presidents’ Day than in the very city where our Founding Fathers signed the United States into existence? We think not. Philadelphia’s rich history, vibrant culture, iconic landmarks, and exploding culinary scene are just a few reasons why this city is so special. 

It’s an excellent destination for all types of travelers: Franklin Institute’s interactive exhibits or George Washington’s birthday party at Washington Crossing are great for families, while a romantic rooftop dinner at the Four Seasons in Center City will appeal to couples. A day trip to Longwood Gardens or Valley Forge National Park never disappoints, which is why a van rental is so convenient. Rent your Philadelphia passenger van today!

Source: Visitphilly.com

2. Williamsburg, Virginia

One of the best Presidents’ Day weekend getaways for families is undoubtedly Williamsburg. Dive into history with an afternoon in Colonial Williamsburg, where actors recreate a vivid image of life in the USA as it was hundreds of years ago. Visit Historic Jamestowne and view archaeological remnants of an early English settlement. When you’ve had your fill of the past, take a short drive to Busch Gardens, where an afternoon of thrilling rides and live entertainment awaits. 

Want to make the most of your Presidents’ Day road trip to Williamsburg? Since there’s so much for families to do in this spectacular state, check out our 11 favorite winter getaways in Virginia.

3. New York City, New York

New York City doesn’t disappoint, no matter the weather. There’s something especially captivating about a chilly weekend in the Big Apple, making it an excellent Presidents’ Day weekend getaway. 

Kids will delight in ice skating at Rockefeller Center and taking in the dizzying lights of Times Square. Couples can stroll the High Line, dine at Chelsea Market, and spend an intimate night out at one of the city’s many jazz clubs. Trying one of New York’s top restaurants after a day at MoMA or taking advantage of Presidents’ Day sales on Fifth Avenue is a great way to spend time with friends. And, of course, a show on Broadway is sure to appeal to anyone of any age! 

Whoever you’re traveling with, New York is always a good idea. But here’s an inside scoop: it’s even better seen by van! Rent your New York City van and get ready to hit the road.

4. Providence, Rhode Island

Providence is cool, quirky, and exciting. It’s an ideal destination for a long winter weekend with friends or your special someone. There are impressive exhibits at the Rhode Island School of Design (RISD) Museum, fascinating walking tours of Providence’s quaint neighborhoods and notable landmarks, and a diverse array of restaurants offering everything from regional clam chowder to traditional Italian on Federal Hill. However, the most magical attraction of all is the annual WaterFire event, starting at sundown, which showcases a series of mesmerizing bonfires that light up the banks of its rivers downtown.

With 400 miles of scenic New England coastline, Rhode Island is a beautiful driving state. We suggest exploring the area outside of Providence if you can. Contact us about Providence van rental opportunities!

Source: Go Providence

5. St. Louis, Missouri

Active families or groups of friends won’t regret a road trip to St. Louis. It’s a beautiful city, with a surprising  mix of modern and historical architecture, leafy tree-lined streets, and Victorian style homes. There’s plenty of activities to keep even the most finicky of travelers occupied: from the famous Gateway Arch and its panoramic views of the Mississippi River to its excellent museums, boredom has no place here. 

Bike along miles of trails or enjoy a picnic with friends at Forest Park. Catch a tour of the St. Louis Cardinals stadium, an experience even a non-sports-fan will love. Unwind in the evening with a good meal or live music in Delmar Loop, a vibrant neighborhood in the heart of the city. 

6. Richmond, Virginia 

When thinking about where to go for Presidents’ Day weekend, don’t forget Richmond. For families, it’s the complete package: history, culture, nature, and great food. 

A must-do for all visitors is the Hearth & Harvest Festival at Historic Richmond Town, where reenactments and historical activities will transport you to the past. Nature lovers will rejoice in statewide Historic Garden Week, which allows access to the most stunning private landscapes and public gardens around. Stroll the Canal Walk together, a path along the river that’s lined with art installations and benches for scenic viewing.

Richmond is an excellent starting point for a road trip. Take advantage of your proximity to the breathtaking Blue Ridge Mountains by renting a van in Richmond and hitting the road.

Source: Richmond.com

7. Lake Placid, New York

Don’t let the joys of winter pass you by! Lake Placid is one of our favorite Presidents’ Day weekend getaways because, even in late February, it’s a guaranteed winter wonderland. Families will have a blast dog sledding across Mirror Lake, tubing at Mt. Pisgah, curling at the Saranac Lake Civic Center, or hiking to the frozen waterfalls at High Falls Gorge.

If you’re traveling by van and have a few days to spare, combine Lake Placid with other New England destinations for a picture-perfect winter road trip itinerary. 

8. Chicago, Illinois

For couples, Chicago is the ultimate romantic winter getaway. It has something for everyone, including theater, museums, architecture, and world-class dining. Lovers can enjoy its spectacular skyline from the warmth of a river cruise or on a bike ride along the shore of Lake Michigan. Perusing the Art Institute of Chicago, one of the country’s best, is always an afternoon well spent. 

One hour west is the historic town of Long Grove. It’s a wonderful respite from the city, a place where you can spend the day wandering its cobblestone streets and popping into its inviting shops. Stop for a happy hour of wine and cheese at Broken Earth Winery before an intimate dinner at The Village Tavern, the only restaurant in Illinois continuously welcoming customers since 1847.

9. Alexandria, Virginia

Traveling with family? Alexandria is an optimal spot for you. Both younger and older kids will find something to like about this historical town outside of the nation’s capital. If the weather permits, head to Jones Point Park or Huntley Meadows Park to wander or have a picnic. You can also rent bikes and explore Mount Vernon Trail and its scenic views of the Potomac River. 

For something warmer, explore the Alexandria Archaeology Museum and the Torpedo Factory Art Center, home to local artist studios and galleries. Don’t skip a walk through Old Town, a charming collection of shops, eateries, and cozy cafes to chat together over a hot chocolate. 

Renting a van even gives you and your family the option to take a day trip from Alexandria to Washington, D.C. (more on that below). Consider combining the two destinations for the ultimate Presidents’ Day road trip!

10. Washington, D.C.

A long weekend in Washington, D.C. is an excellent destination for families, friends, and couples. This thriving metropolis has something for everyone to love. It’s home to the world’s top museums and renowned monuments like the Lincoln Memorial, the perfect backdrop for your group selfie. 

The Kennedy Center offers a wide range of theater, dance, and music shows. Exhibits in the Smithsonian and the National History Museum are guaranteed to impress even the most finicky teen. In addition, D.C. is just a short drive from George Washington’s Mount Vernon, a quintessential way to celebrate the founding father’s birthday! 

Traveling to Washington D.C. with a large group of family or friends? Make the trip easier and travel together! Rent a van from Greenvans in Washington, D.C.

Source: Fairfax County Virginia

11. Springfield, Illinois 

The state capital of Springfield is an obvious stop on a midwest road trip, especially over Presidents’ Day weekend. After all, it’s the birthplace of the 16th U.S. President, Abraham Lincoln! 

Take a tour of his well-preserved home before embarking on a short ride to Oak Ridge Cemetery, Lincoln’s resting place. If you’re looking for good luck, rub the nose of the statue situated at the cemetery’s entrance. Kids learning U.S. History will appreciate a visit to the Abraham Lincoln Presidential Library and Museum for an in-depth explanation of his life and campaign.

While there’s plenty of upscale dining in Springfield, you’d be remiss to leave before sampling the Horseshoe Sandwich, a local favorite stuffed with meat, french fries, and smothered in a cheese sauce. Following it up with a stroll together in the city’s lovely park district is definitely the right call.

12. Boston, Massachusetts

Boston is chock full of things to do all year long, so it’s no surprise that it made our list of the best Presidents’ Day weekend getaways. Families, friends, and couples will have a blast at the Boston Common Frog Pond, where you can go ice skating for free. If you’re traveling with your kids, take them to the New England Aquarium for all things aquatic: explore the exhibits, watch 3D nature documentaries, or bundle up for an unforgettable whale-watching cruise!

For those celebrating a belated Valentine’s Day, sign up for a romantic Boston Harbor cruise. There are great breweries and pubs for friends to hang out and sip on craft beers. If you decide to rent a van in Boston, you can take advantage of Boston’s proximity to Martha’s Vineyard, Plymouth, or Salem for a day trip with your travel companions.

Source: Meet Boston

13. Keystone, Colorado

Not ready to give up on snow? Winter lovers will get a kick out of a long weekend together in Keystone for its excellent skiing and snowboarding opportunities. After a day on the slopes, unwind in charming Keystone Village to shop, stroll, and feast. Or, you can opt to spend the day downtown and the night at Keystone Resort, which offers night skiing on select dates throughout the season! An experience like this will surely be unforgettable.

Keystone is within driving distance to some of the most iconic locations in the U.S.. The quaint ski town of Breckenridge is close by, as is Leadville, from which you and your crew can hop on a scenic train ride through the San Isabel National Forest. Colorado’s landscapes are spectacular, and the best way to enjoy them is from the comfort of a warm, comfy van.

Things to do on Presidents’ Day weekend

Regardless of where you decide to spend your Presidents’ Day weekend and with whom you decide to spend it with, there’s no shortage of things to do to celebrate. Whether you’re holding on to winter or eagerly anticipating spring, here are some ideas to satisfy every travel palette.

If you’re celebrating the last days of winter, we suggest: 

  • Skiing in Colorado with your friends
  • Ice skating in New York or Boston with your lover
  • Dog sledding in Lake Placid with your family

If you’re celebrating the country’s fascinating history, head to:

  • The Liberty Bell in Philadelphia
  • Colonial Williamsburg for a step back in time
  • The home and resting place of Abraham Lincoln in Springfield 
  • The monuments of Washington, D.C. and Old Town Alexandria

If you need a creative spark, we think you’ll like:

  • A spin through Rhode Island School of Design (RISD) Museum in Providence
  • An afternoon in the Art Institute of Chicago
  • Touring the magnificent gardens during Historic Garden Week in Richmond

If you’re in search of spring, why not visit:

  • Williamsburg, an optimal jumping-off point to explore the beauty of Virginia and the Blue Ridge Mountains

Long weekends are better with Greenvans

A long Presidents’ Day weekend getaway with your favorite people guarantees lifelong memories. No matter what you and your travel companions are yearning for — art, sports, history, or food, it will be easy to find by renting a van and hitting the road. 

The team of experts at Greenvans can set you up with a spacious, secure 15-passenger van, ensuring the utmost comfort as you and your clan make your way around the country together. But we’re more than just a van rental agency. We also offer ideas and advice to optimize your travel plans, as well as 24-hour assistance while you’re on the road.


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