Growing up, West Point had never been a destination. It was the halfway point between home and Richmond, an occasional away game for high school athletics and the marker of the last leg of the trip coming home from college.
Little did I know what a charming and vibrant small town community nestled just the other side of bustling Route 33. Packed with darling boutiques and antique shops, impressive restaurants and outdoor recreation and adventure, West Point is the quintessential coastal small town, hidden gem that everyone should explore.
“Three Rivers, Two Bridges, One Special Place,” serves as the defining mantra for the Town of West Point. This small peninsula community of about 3,500 residents sits at the confluence of the winding Pamunkey and Mattaponi rivers, which merge at the tip of the town to form the expansive York River. Over the centuries, the waterfront geography has transformed West Point from a vital Native American stronghold into a bustling center of commerce and industry.
Researching
There was no better place to begin my West Point adventure than at the Historical Society of West Point. The two story museum celebrates the Town’s earliest beginnings and showcases local heroes. From displays showcasing the very first settlement on the land predating the1600s to its ultimate transformation to a resort destination in 1887 all the way to celebrating modern school athletics history, West Point’s fascinating history is well chronicled throughout the museum.
Joanne Wright, an associate with the museum, guided me to the displays that would help me form a sense of understanding on how West Point came to be what it is today.
When I arrived in the museum, I was greeted by displays showcasing the town’s earliest days. West Point was originally the Indian village of Cinquoteck used by the Powhatan Confederation. Historic artifacts like arrowheads and stones sharpened down to knives that were known to belong to the tribe are on display.
Joanne told me it is important to understand how West Point got its name. In 1653, Captain John West, the former Governor of Virginia from 1635-1638, patented 3000 acres including the area of Cinquoteck and the Eastern part of the Neck. By 1691, a town began to take hold at the site of West Point to serve as a tobacco port. Established in 1701, the town was named Delaware Town after Thomas West, also known as Lord Delaware. Thomas was the older brother to John West, and also served as Governor and captain-general of the Virginia colony from 1610-1618.
In 1853, the Richmond and York River Railroad was formed and was completed by the time the Civil War rolled around. The town became an important transport hub and strategic entryway towards Richmond. Due to its location and homage for the West family, the site officially assumed the name West Point in 1861 once the railroad was complete. The Union eventually took over the town in 1863 and destroyed the railroad. It was rebuilt a year later. In 1870, the West Point site was incorporated.
Over the years, West Point witnessed drastic change, from agricultural endeavors to eventually becoming a hub for steamboats. With the construction of the Terminal Hotel in 1887, West Point became a major resort destination overlooking the three rivers and was outfitted with a boardwalk, skating rink, dance pavilion, roller coaster and even a gambling hall.
By 1918, Chesapeake Corporation was formed and had taken over the mill that had been constructed just a few years prior. Initially the mill was used to supply container board and paper for World War I. Today the facility operates under Smurfit Westrock and employs about 1,000 workers.
Chatting
ChattingAfter gaining an understanding of West Point and its history, it was time to explore all the town has become. It was a gorgeous day, so I knew a bit of outdoor adventure was on my itinerary. Before really diving in to the day, I had to fuel up with some breakfast.
In the heart of Main Street is a cute cafe called The Pie Lady and Company. I stopped in and was greeted by Crystal Burch, the owner and Pie Lady herself.
Crystal opened her doors in 2023 and has been a community staple ever since. Of course she offers delicious homemade pies and desserts, but also hearty breakfast and lunch items, too.
She said her breakfast sandwiches are always a hit. I trusted her and ordered myself a tried and true classic, a sausage, egg and cheese biscuit.
“It’ll take me a few minutes, I’m making the eggs to order,” she said.
A little wait time is always worth it when something is prepared with care and love. And boy did that ring true. Perhaps served on the softest biscuit I’d ever tried, my breakfast sandwich totally hit the spot. Crystal told me I’ll have to come back for lunch one day and try her chicken salad—a local favorite.
As I was speaking with Crystal, I got a real sense that West Point is a community that always put its people first, and that residents have a true pride for where they call home.
As she’s seen more people move to the area, she’s been very pleased to see that people have adapted to the town’s culture, rather than trying to change West Point, said Crystal.
West Point is filled with older homes, all beautiful and charming, and they really play a crucial part to the neighborhood feel of the community, continued Crystal. She’s been pleased to find that as more people continue to move in, they’re maintaining and restoring these older homes instead of replacing them with modern manufacturing.
Crystal also said that within the business community, everyone wants to see each other succeed. She said as more restaurants appear in town, she doesn’t feel threatened—there’s enough to go around. Sometimes when a new restaurant opens, she may have a slower week as everyone wants to give the new place a try, but it all evens itself out. With more options comes more people, and everyone wins, she said.
Browsing
Crystal said that some shops, like The Exchange on Main which sells antiques and vintage merchandise, are only open on the weekends so I’ll have to come back to explore all Main Street has to offer. She did send me off with a recommendation to stop in at Divin’ Off the Dock, a fun boutique just right down the street.
I began my walk down Main Street, almost feeling like I had stepped back in time. Kids were out riding bicycles, older gentlemen were stopping into the old-school barbershop and the storefronts maintained a classic Americana feel to it.
I came across a mural in the center of town. The beautiful mural was unveiled just last summer, and it’s the town’s first official Virginia LOVEworks sign.
The mural, which was painted by Michael Rosato, celebrates the rich heritage of the town. Connected by a couple of bridges with the water as the forefront, the mural highlights the Native American roots, showcases a fun history as an old steamboat port, and even shows love to modern day traditions like the famous Crab Carnival. Fit with a gazebo and benches, residents and visitors are urged to take a moment to enjoy West Point at a glance through an artist’s eyes.
When I made it to Divin’ Off the Dock, I instantly knew this place was no good for my wallet. I kept finding home accessories I knew my Granny would love, perfect housewarming gifts for friends that are about to make a move, and the most adorable pair of jeans I think I had ever seen.
I met the shop owner, Beth Kelley, who said she and her family had owned the shop since 2009.
“We’re a coastal boutique specializing in all things home, fashion and rivah,” she said.
Beth said the inspiration for the shop and it’s name stemmed from her family’s leap of faith in opening up the boutique, and is a nod to her family’s river heritage and enjoying the waterways as a kid.
If you’re interested in shopping til you drop, a weekend afternoon spent walking up and down Main Street can help you get your shopping fix. With other spots like Homestead Cottage and West Point Antiques, there’s something for everyone.
Around town there are a number of historical markers highlighting iconic locations from days before. The museum offers a map to track all 31 markers. It’s almost like a self-guided walking tour, and is a great way to gain appreciation for where you are.
Kayaking
After perusing Main Street and other side streets, I took my adventure to the water. Almost right behind the McDonald’s in front of Main Street and off of Route 33 is a public water access kayak launch. There’s even a kayak rental kiosk.
Once I launched my rental kayak into West Point Creek, I was paddling through the winding creek surrounded by tall grasses. I passed a couple of crab pot buoys and docked skiffs right along backyards, proving the working waterfront is alive and well in West Point.
After several minutes of paddling West Point Creek I had reached the Mattaponi River right beside the West Point Mattaponi River Bridge. Though the bridge had non-stop cars driving over it, on the water I was the only human as far as the eye could see.
I took a right and paddled along West Point’s waters edge. Plenty of different species of birds were all around. Fish were jumping left and right. The water was so calm, yet so alive with wildlife, all while right beside town.
I paddled nearly an hour one way, admiring the gorgeous waterfront homes. I had made it to the Pamunkey River when I spotted the Eltham Bridge. At this point I could also see the paper mill in the distance. There were inlets in the distance I was dying to explore, but I knew I only had a little more than an hour left in my rental so I decided to turn around.
One could easily make an entire day of surveying the area by water and counting the many different species of birds. Next time I come to West Point, I’ll definitely have to bring a fishing pole. Anglers are known to often catch largemouth bass, striped bass, blue catfish and red drum in the waters. There’s a dedicated fishing pier on the other side of town at Glass Island Boat Landing for easy access to reel in a fish.
By the time I got back to the kayak launch, I had to cool off from the summer heat. I headed to “Kiss my Ice eeee” on Kirby Street for a slushy.
The place was adorable with a vintage ice-cream parlor vibe. Neon signs and antique cola memorabilia lined the walls. They serve their slushys in giant Chinese food containers, adding all the more charm to the treat.
After exploring West Point by foot, car and kayak, there was just one other vantage point—from above.
Skydiving
For years I had always passed by the office to No Limits Skydiving and always told myself, “I’m gonna go skydiving one day.” That day had finally come.
The journey began just outside of West Point, where waivers were signed and gear was fitted, before we made our way to the Middle Peninsula Regional Airport. There, we boarded a small plane, ascending into the quiet sky with my tandem partner, Joseph Hallacy. Joseph has been skydiving for 39 years.
“After all this time, do you ever still get nervous?” I asked.
“Nope,” he smiled. “I just love it more and more.”
He shared that earlier that afternoon, he had helped a 70-year-old lady check skydiving off her bucket list. There is no age limit to chasing a dream here; so long as the body is willing and agile. Having jumped all over the country, Joseph insisted that West Point offers one of the most breathtaking views. Looking down, it was easy to see why. The three rivers twisted and turned like shimmering ribbons through the landscape, bordered by endless stretches of green fields and old farmland. It felt less like reality and more like an illustration from a storybook.
After 10 minutes of flying, the door opened. Joseph secured the harness between us and repeated his final, simple instructions: right foot inside of his on the outer ledge, arms crossed tight, and let go of everything.
Before fear could catch up with me, I was tumbling out into the open air from 12,000 feet.
The late afternoon sky was painted in rich, golden hues, casting a serene light over the world below. The water glistened and the trees looked incredibly green from our high vantage point. For one full minute, time entirely stood still during a freefall of pure, unadulterated exhilaration.
At 5,000 feet, the parachute deployed with a sudden pull, and we drifted gently for five quiet minutes. Strangely, the canopy ride felt even more surreal than the fall. With the wind rushing past, I could actually feel my heart pounding as I began to recognize the tiny landmarks of the town I had spent the day exploring. I couldn’t shake the wide, childlike grin from my face.
“Is this one of the craziest things you’ve ever done or what?” Joseph shouted over the wind.
As our feet touched the grass in a perfectly soft landing, Joseph noted that the jump couldn’t have been more flawless. The lighting, the air, the timing had aligned beautifully. If you’ve ever had the urge to make the jump, do it. It is a liberating, wild kind of freedom that stays with you, a reminder of what it means to truly feel alive.
Unwinding
With adrenaline still buzzing through my veins, hunger was the furthest thing from my mind, but I desperately wanted a cold drink to toast the end of an unforgettable afternoon. When I asked Joseph where the locals went to unwind, he pointed me toward the other side of town, to a modest little pub known as Lovell’s Place.
When I walked in, only one bar stool was left. The crowd occupying the bar consisted of older regulars who clearly owned the space.
I sat next to a gentleman named Wilbur, who affectionately went by the nickname “Keg.” He told me he was from West Point and was retired military. His favorite part of his day is picking his grandkids up from school, who happen to live just a few houses down from him.
He said after growing up in West Point, he branched out a bit and lived in places like Pittsburg and Chicago.
“Eventually I just got pulled back in. This is home,” he said.
Everyone knew everyone here. Some were old classmates, others were neighbors separated by generations. It reminded me of walking into a familiar spot in White Stone, where every face is a friend.
I enjoyed a beer as Keg told me about the sports he played in high school and I asked him a bit of what it’s like to live in West Point. His answer was simple: he lived in a waterfront town with his wife of many years, sees his kids and grandkids every day, and volunteers to help senior citizens in his down time—what’s not to love?
As I finally headed out from Lovell’s, known as “The Best Joint in West Point,” and began working my way home, I couldn’t help but think of what a full and fulfilling experience I had. Everywhere I went people were more than kind and happy to talk with me and share what it meant to be from West Point. I was surrounded by natural beauty and a charming downtown, took a literal leap of faith, and all the while made connections that lingered long after I left.
West Point is not a place you simply drive through; it is a sanctuary where time slows down.
It is a true hidden gem, patiently waiting in plain sight. The next time your driving app routes you through its borders, pull over. Stay awhile. Enjoy what community feels like.
