7 Picturesque Stops for Snowbirds Driving South

Are you planning a road trip or RV adventure to Florida and wondering which stops along the way are genuinely worth a visit? Look no further! Explore these seven charming small towns that will captivate you while immersing you in the essence of American culture.

These destinations will delight those looking for more than a simple journey along Interstate 95. You can stop for a few hours to several days, depending on your interests, budget, and the time you have available.

So, turn your ordinary road trip south into an autumnal adventure with these seven must-visit destinations:

1. The Berkshires, Massachusetts

While driving south, consider stopping in the Berkshires, a region historically favoured by Boston's elite as a summer destination, drawn to its natural beauty and undeniable charm. Autumn is a magical time to visit The Berkshires. A true symphony of colours unfolds before you along the way. This Massachusetts enclave comprises 33 villages, and here are some of the most interesting to visit from north to south:

• Williamstown is an enchanting college town centred around Williams College, with many cute cafes exuding a relaxed and intellectual vibe.
• North Adams presents itself as a revitalized, youthful, and artistic town that proudly claims to be the smallest city in Massachusetts, attracting artists and creative minds from all around.
• Lee is a warm, more affordable, and diverse town in one of the wealthiest areas of the Berkshires.
• Lenox is famous for its elegance and distinction, housing some of the Berkshires' most renowned sites, along with a picturesque and charming atmosphere.
• Great Barrington stands out as an urban destination in nature, offering a pleasant pedestrian ambiance and an ideal setting for relaxation and good times.
• Stockbridge embodies the quintessential New England small town, straight out of a fairy tale, with its quaint streets and timeless charm.

Enjoy hikes in the maple forests with their orange hues and be charmed by the Berkshires' rustic yet sophisticated allure.

2. Gettysburg, Pennsylvania

Take the time to stop in this small historic town, famous for the iconic battle of the American Civil War: the Battle of Gettysburg. This battle marked a decisive turning point where the pro-slavery and secessionist Southern forces suffered a major defeat against the Northern Union and abolitionist defenders.

Start your visit at the Gettysburg National Military Park Museum & Visitor Center to learn more about the history of the place before embarking on a self-guided exploration of the vast battlefield. Download this free audio guide for more information on each stop, including the magnificent Pennsylvania Memorial and the National Cemetery, where Lincoln delivered his speech in 1863.

In the evening, head to Lincoln Square, the heart of this charming town with its brick buildings, and dine at one of the numerous restaurants and breweries.

For a unique experience, seek out the Reliance Mine Saloon, a bar accessible through a mysterious wooden door hidden behind the Quality Inn Gettysburg Battlefield Hotel. Descend underground to discover a pub with a cozy fireplace offering affordable drinks and immersing you in a rustic atmosphere reminiscent of the mining era.

3. Williamsburg, Virginia

Delve into American history in Williamsburg, where autumn adds a touch of magic to the colonial ambiance. Famous for its role in the American Revolution, Williamsburg served as the capital of the Virginia Colony from 1699 to 1780.

Take the time to explore Colonial Williamsburg, a vast historic city spanning 301 acres in the heart of the town. Plan a full day to explore this site, which is considered the largest outdoor history museum in the United States. Here, you'll encounter costumed characters reenacting scenes from 18th-century daily life amid period buildings and churches.

In the evening, dining in one of the city's historic taverns is truly one of the most unique experiences in Williamsburg! Be sure to make reservations at least two weeks in advance, especially for places like Christiana Campbell’s Tavern  (George Washington's favourite for seafood) or the King's Arms Tavern.

4. Asheville, North Carolina

Make an enchanting stop in Asheville, North Carolina, ranked among America's "most beautiful small towns." Nestled in the Blue Ridge Mountains, Asheville is surrounded by state parks, hiking trails, and majestic waterfalls. Autumn offers a stunning display of a dense forest transformed into a mosaic of reds, oranges, and yellows.

Stroll through downtown Asheville upon arrival, a lively pedestrian neighbourhood with pubs, trendy restaurants, art galleries, bookstores, and street artists awaiting your visit. Let yourself be charmed by the eclectic style of this unique city.

Explore the colourful River Art District to discover the artistic treasures of over 250 local artists.

Be sure to visit the famous Biltmore, the largest private estate in the United States, before leaving Asheville.

5. Charleston, South Carolina

Head to vibrant Charleston! This city that exudes timeless elegance will dazzle you. Take a leisurely walk along iconic streets like King Street and Meeting Street, lined with antebellum houses in vibrant colours. Discover the city's beautiful gardens and historic parks, including the famous Waterfront Park, where you can relax near the giant pineapple fountain, an iconic image of Charleston, while enjoying breathtaking harbour views.

Don't forget to visit the Charleston City Market to find local products and unique souvenirs. Charleston's cuisine is an experience in itself. You can savour local dishes, fresh seafood, and Southern flavours. Try local specialties like gumbo, shrimp and grits, as well as delicious whole-grain biscuits.

Music also plays a central role in Charleston's life. You can enjoy live jazz, blues, and Southern Soul music concerts in many of the city's bars and clubs. The lively Southern rhythms create a warm atmosphere, inviting you to dance and unwind.

6. Savannah, Georgia

Spend some time in captivating Savannah, Georgia, a delightful destination in autumn. Its streets lined with majestic Victorian homes adorn themselves with garlands of golden leaves. 

Stroll along River Street and explore its museums and parks, all while soaking in the unique atmosphere of this historic city. Plan your visit with this guide to Savannah's must-see attractions for Snowbirds.

7. St. Augustine, Florida

Wrap up your fall expedition in St. Augustine, a delightful city in northern Florida that holds the historical legacy of Spanish influence in North America.

Visit the Castillo de San Marcos National Monument, wander through the cobblestone streets of the old town, and enjoy the mild autumn weather on the white sandy beaches. Discover why you must visit St. Augustine, the oldest city in the United States.

Take the time to stop along the way!

Each of these picturesque stops offers its own range of unforgettable experiences in the fall. You now have all the information you need to turn your trip into a memorable itinerary with these seven picturesque destinations. 

Whether you're passionate about history, nature, culture, or simply seeking an authentic experience, these stops along the way to the South offer something unique that's well worth the visit. Discover the most beautiful routes to Florida.

Enjoy your journey in the United States and explore hidden treasures along your route. Contact a soNomad agent to find the best travel insurance for Snowbirds.