What was your happiest moment in Williamsburg, VA?

Featuring a man walking a pig on a leash

Williamsburg is known for its rich American history as well as its beautiful nature and scenery. I went to one of the most well known locations, Colonial Williamsburg, and talked to as many strangers as I could about their happiest times here and tried to find out what exactly makes this town so special.

Ryan Philips

As soon as I arrived in the colonial area, I spotted across the street a man walking a pig on a leash, so naturally that had to be my first stop. The man’s name is Ryan Philips, he is 39 years old and he is an animal activist.

I asked Ryan about his happiest time in Williamsburg and this is what he told me:

“It would have to be walking around Colonial Williamsburg. You feel like you are not part of the world for a while because it’s so removed from the stresses of modern life, and everyone around you is dressed up in the clothes from a different century, it’s all so surreal it’s like being in a different world for a minute. My favorite memory here had to be my first date with my wife, we went to the old haunted jail house and hung around there and it was magical. Other than that, I love bringing Charlotte (the pig) down here and just hanging out with her and letting other people meet her, it’s a great way to spend your days.”

Group of kids from Bruton High School

My alma mater! I came across these kids who couldn’t keep themselves from giggling the whole time, and as soon as I’d finished interviewing them they all bursted into laughter.

Kale, 15 told me about the time he got baptized.

“The time I got baptized on the James was pretty cool! I was at church and they said they were going to do some baptisms at the river, and I’ve always been believin’ and I’ve been a believer so I thought I should take that next step and make it baptized-official *bursts into laughter* It was pretty spontaneous actually. We all hopped on the bus and I was kind of nervous, and they took us down to the river and I remember the water was cold, and they just did it. And then we were eating hamburgers and hotdogs and it was a good time, and I had this happy feeling like I did something right and I was that much closer to God and to heaven.”

This is Jonah, he is 16.

“I like coming out here to Colonial and petting every dog I come across. It’s always a good day when I can pet at least five dogs. I like having lunch at the Governor’s palace too! This one time when Pokémon Go just came out I came here with my friends to hunt Pokémon and we were walking around here just laughing together and joking on each other, we even stopped to get ice cream and it was a lot of fun. Colonial Williamsburg has some good rare ones so that was a good place to play Pokémon Go!”

16-year-old Mackenzie said “I love working down here at Killan’s ice cream! My favorite times are when the line gets really long like all the way out the door and I just get this rush of adrenaline. Plus I’m close with my coworkers so when it’s not busy we are in there joking around and laughing at stupid stuff, it’s weird to love your work I guess but those are my happiest times in Williamsburg!”


This had to be the coolest thing I’ve ever seen. This dude was blowing humongous bubbles and he had a crowd forming around him, so of course I rushed over there and spoke to him while he was doing his thing!

His name is Stefan, he’s 31 and currently unemployed, “a professional bubble blower” he joked! Said sometimes he puts out a hat and gets loads of tips.

When I asked him about his happiest memory here in Williamsburg, he said “Interesting, well I grew up here and moved away about ten years ago and I’m just visiting for the week but I always loved hanging around Colonial Williamsburg. Oh I know a good one, this one time I came here and I was hanging out over by where the toy store used to be making my bubbles and there were a bunch of kids that day and on every one of their faces you could just see the look of awe. There’s nothing that gets such a universally positive reaction, like everyone that walks by loves to watch the bubbles and it’s so easy to do! It’s like a little bit of magic you can bring to your day with barely any effort and it makes everyone smile.”


I met Devon when I was grabbing a Chai Latte from Aroma’s, a local coffee shop beloved by the William and Mary and Williamsburg community. He was leaning against this sign that said “Unattended Children will be given an espresso and a free puppy,” to which he complained, wishing he was an unattended child.

Devon told me about his happiest memory, “I’d been living in Williamsburg for a big part of my life and honestly kind of hated it. I thought it was this hole where people get stuck and they don’t ever like it but they never leave, but then I moved to LA and I came back to visit six months later and finally I was able to see the beauty of this place, I just needed a little distance to really understand it. I was driving with a friend on the parkway, and it was in the fall so all the leaves surrounding the cobblestone were orange and red and it looked like the trees were going up in flames and just all the nature and the history, for once I realized what was so beautiful about Williamsburg and I just kinda fell in love. It took a fresh eye for me to really understand but all this beauty had been right under my nose for years. I’m glad I got out so I could come back and be awestruck. That had to be my happiest memory here.”

Gail and Ruth

Gail on the right told me she is retired but now sells stocks on the internet and that’s her idea of fun.

When I asked her about her happiest time here she said “We had a family reunion here a few years back and my husband is one of ten siblings so all the family came up here from around the country and my favorite part, we went to Waller Mill park and all the kids were just running around shooting their toy muskets they got from CW, and they were just so happy to be running around with the whole big family. We had cookouts and talked about all our shared memories together and it was so wonderful and warm to be with all the people we love.”

Ruth on the left told me her profession was to raise the babies, and when I asked her about her best time in Williamsburg she said “Oh I’m not as exciting as Gail. My best memory is just like her with all the kids down and we live on the river so all the kids come in and swim around.”


I met 18-year-old Rhett while she was sitting outside of Aroma’s with coffee in hand.

She told me “My happiest time here is those nights during the golden hour where I chase the sunset with some friends. We keep the windows down and smoke and listen to the kind of music that you can really feel and search for the best places to watch the sun go down. But that golden glow from the sun starting to dip is my favorite, it’s not even about the actual sunset it’s just the warmth and the light as the day starts to close, I love it. My favorite place we have caught the sunset is out by the James river though, if you climb out on a dock, you can really be surrounded by it. Also those spots off the Parkway towards Jamestown where there’s the hidden beaches, the sun sets a little out of sight but you get all the watercolor sky sights and the whole thing is great. That’s when I’m the happiest.”


David told me he’s “too old” at 87, and he said he was a police officer for 32 years, and did the same type of work as a security guard. And now for 35 years he’s been doing part time at Farm Fresh.

His happiest times, he said are “Bringing this dog up here, she loves people. I got her from Houston, Texas, she’s a rescue. I found out she’s real good with people and children. So my wife passed almost six years ago in October, and so when she passed I told my daughter, you gotta move home and she said ‘I’ll do even better, I’ll get you a dog.’ and so she got Sadie. And this is a really good deal, she doesn’t talk back, and she gives me all the love and affection I could handle, and she is smart as a whip, when she don’t wanna be smart she’s a handful. But she’s a good girl. She brings me the most happiness I could handle. She just got out of the stage chewing up all the stuff in the house haha.”

We all know dogs are the best source of happiness, but this guy really had the proof! Sadie and him are the perfect match!


Tre, 18 told me his best memory here is “Probably when we went to Don’s after party on Halloween. I was a senior at Bruton high school and me and a bunch of kids went over to his house and we were drinking beers and laughing about high school and we were having a great time. It was a good way to start off our last year, a good way to close off our high school life I guess. I got to hang out with all the people I had grown close with over the past years, and I’m kind of sad to have it end but I’m excited to see my next chapter of life. So that was my best night, realizing that I had had a great first part of my life and becoming excited for what’s to come in the future.”


Hannah is an 18-year-old rising sophomore at William and Mary and she said “My best time in Williamsburg so far…probably my last night at orientation, because I just settled into my new dorm room and me and a couple of friends I made during orientation went walking around Williamsburg in the dead of night and we were being hoodlums, it was like 3 am and we just walked up and down the strip and it was just so beautiful being there at night and having all these fires around because it was winter, and that was when I knew I had picked the right school I was going to be spending the next four years at. I made some great friends, was already collecting these awesome memories with them, and it really just got me excited for the future!”


Talking to all these different people was great because I got to hear what was special to each of them not only in Williamsburg, but in their lives. There were some things all of them had in common- their happiest times included love. From Ryan and his pig and his wife, to David and his beloved Sadie, to the old women with their big families and grandchildren, they all remembered most the times when they were surrounded by love as their happiest times.

Everyone was also pretty fond of Colonial Williamsburg, and can ya blame them? A rich history and some beautiful nature and buildings is enough to make anyone swoon with love and happiness!

The Tab Local