Modern Travel: Small Town Charm in Alexandria, Virginia

a cobblestone road leading toward the potomac River in alexandria, virginia.

Historic, not stoic.
As an entrepreneur for over 15 years with an education in marketing and advertising, it’s one of those lines I wish I came up with. It’s a city steeped in history and forward-thinking. All credit goes to Andrew Postal, Director of Communications for Visit Alexandria, who clearly deserves a raise.

the majestic waterfront in alexandria, virginia.

Located in Northern Virginia, Alexandria has a big-city feel draped in small-town charm, all with a population of approximately 160,000.
There’s historic brick sidewalks lining the King Street Mile, or for me, the King Street 1.6 kilometre. There’s over 200 independent boutiques and restaurants. There’s a stunning waterfront paired with a natural, inviting ambiance. Immerse yourself in activities and adventures or slow down and soak in the views by foot or on one of several places to sit and relax. 

the view from the edge of the boardwalk in alexandria, virginia.

As a professional travel writer and videographer with over a decade of journeys, Alexandria has earned my “I’ll be back a few more times at least” status.

Use this as a guide for things to do in Alexandria, Virginia, or create your own itinerary with pieces of my experience.
Here, I’ll share the highlights of my two short yet satisfying days in this splendid city that’s only an eight-ish hour drive from Mississauga/Toronto, or a hour-ish direct flight into Washington’s Dulles.

the hilton old town is perfectly located to maximize the very walkable city of alexandria, virginia.

Let’s start with setting up your home base, which for me, was the Hilton Alexandria Old Town at King Street and Daingerfield Road. My room was spacious, the bed was oh-so comfortable and the customer service was above and beyond. Free wifi and its ideal location make it a smart place to call home.

the free king street trolley in alexandria, virginia.

Being a very walkable city, keep your car in the hotel’s underground parking and use the free trolley or free city bus services.
Side note; free transit makes good cities that much better.
The transit hub is across the street from the hotel and you’ll spend more time waiting for the traffic light to change than you will to walk to the trolley.
The vintage styled trolley is the way to go as it’s fully modernized inside, has a frequency of every 15 minutes between 11:00 a.m and 11:00 p.m. daily. Plus, it stops every two to three blocks!
Another side note: there’s an Amtrak station across the street from the hotel.

the pedestrian only area of king street in alexandria, virginia.

On a Saturday afternoon, my travel companion, Nancy, and I took the trolley to the end of the line, being the pedestrian only area of Old Town. The weather was in the high 20’s, the sun was shining and the place was buzzing. Live entertainment, a plethora of patios with people smiling and dining. An array of ages and cultures filled the spaces. Simply put, there’s so much pizzaz here. It’s vibrant, approachable and inviting for everyone. 

homemade ice cream from the creamery in alexandria, virginia.

We stopped for ice cream at The Creamery, which is Alexandria’s longest running ice cream store at over 40 years. I opted for butter pecan and I’d do it again, it was that good. The line was long but moved quickly and a few minutes later, we were outside with waffle cones in hand taking obligatory ice cream pictures.
Another hot spot in the city is Jeni’s Splendid Ice Creams, about halfway between the water and the hotel. It’s open late, the flavours are creative and the vibe is cool.

a musician serenades onlookers in old town alexandria, virginia.

Strolling down to the waterfront saw more live music, including a guitarist about half my age and a dozen times more talented performing a thunderous version of Purple Rain by Prince. 

Walk along the waterfront to soak in the views or take a seat at one of the many public seating options, including an “S” shaped bench that we stopped at. With me being a Pisces and Nancy an Aquarius, we found a spot on the bench and admired the subtle waves and watercraft gliding along the Potomac River.

these feet were put to good use in the walkable citiy of alexandria, virginia.

If you can, grab a seat on any of the patios because yes, food and drinks taste better outdoors. We made a quick stop for pre-dinner appetizers on Blackwall Hitch’s patio before walking it off with a 10-minute jaunt to the famous Hollensbury Spite House, measuring a mere seven-feet, six-inches wide and a cozy 350 square-feet.

the Hollensbury Spite House in alexandria, virginia.

A cotton candy sunset was our backdrop as we sauntered from Queen Street back to King, admiring the tree-lined neighbourhoods, year-round lights on the King Street trees (how festive!) and the overall charismatic feel Alexandria delivers. 

josephine, a french-inspired restaurant in alexandria, virginia.

“Real” dinner was at the popular French-inspired restaurant, Josephine, housed in a historic 1883 firehouse building, complete with a compilation of tiny details that collectively bring the interior to life. It’s dimly lit, emulating an enchanting dining experience where the you appreciate the intimacy surrounding you.

beautiful brick sidewalks in alexandria, virginia.

Another slow and meaningful walk back to hotel showed off Alexandria at night, which still buzzed with excitement and activity with a different backdrop.
The glow of the streetlamp fell against the brick sidewalks, the mild car traffic echoing against shop windows. Filling the gaps were the soft sounds of our running shoes gracing the pavement in tandem. We reflected on our day and how special Alexandria’s aura is. We’d been on the move since the early afternoon and through everything we experienced, we knew there was so much more to explore on another visit.

misha’s coffee, complete with stellar service in alexandria, virginia.

The next morning, we took another short walk to Misha’s Coffee, a local joint with the best customer service I’ve had in a coffee shop. Ever. The two jovial ladies behind the counter at 8:55 a.m. since a small “We’ve got first-timers!” song to us! And they were friendly, engaging and it felt like we were having a conversation with old friends. 

the mansion at george washington’s mount vernon.

Fully caffeinated, we set out for the George Washington’s Mount Vernon, courtesy of a scenic 20 minute drive along the George Washington Memorial Parkway.
You’ll get plenty of steps in here so be sure to bring a reusable water bottle.
The mansion tour is a must, the gardens are beautiful and the overall experience is a piece of history worth experiencing. 

tell boomer jay & nancy from canada say hi when you visit chalkboard wings & bbq in alexandria, virginia

We needed lunch after all those steps and tucked away in a strip mall a mere seven minutes away was my favourite dining experience, courtesy of Chalkboard Wings & BBQ. Yes, the wings were perfect but what made it so memorable was the service. Our server, Boomer, an absolute wonderful woman, was friendly, engaging, kind, and most of all, she laughed with us. And she laughed. And we laughed. The food could have been average and it still would have been my favourite food spot in the city. 

The balance of the afternoon was spent with me filming our road trip chariot, the 2026 Mazda CX-90. You can use it as downtime or additional adventure time, or to get more ice cream.

thompson italian serves up wonderful handmade pasta in alexandria, virginia.

The final stop on our whirlwind Alexandria tour was Thompson Italian, featuring delectable handmade pastas in an energetic dining room. The smartly small menu (because multi-page menus create analysis paralysis) had enough of a selection to likely make most people happy.

As I write this, I realize how much was packed into such a short time period. It didn’t feel rushed, though. It felt natural. It flowed the way it was supposed to and I wouldn’t change anything about it.

old town in alexandria, virginia has a bustling, complete waterfront.

Alexandria is well-deserving of its 2025 Travel & Leisure Top 5 City in the US award and its 2025 Condé Nast Traveler Top 3 Best Small City awards. I’ll throw in my own Modern Traveller award for Alexandria being on my exclusive must-return-to-at-least-twice award.

There’s plenty of progress happening here and the city certainly isn’t standing still.
This small city has made a large impact and it’s one that should be experienced at least once, ideally thrice. 

Head to visitalexandria.com to start planning your adventure.

slow down an soak in the potomac river in alexandria, virginia.