our second anniversary, williamsburg in october

After embracing the classic anniversary gift of “paper” last year (at the casino), I really wanted to continue the unique tradition and plan a trip around whatever the second classic anniversary was. I saw it was cotton and got excited, thinking we would easily be able to find someplace great nearby. As I did more research though, I started to get really turned off by the idea. Eric and I love history and have been to several cotton fields, functioning gins, and old plantations on field trips through the years, so we’ve seen that history up close and personal. The idea of willingly taking a vacation to a historical plantation with such a negatively charged history behind it (which they all do in some way or another) didn’t really seem romantic to us. It’s sad and important, but not romantic. We did however feel inspired by the idea of doing a more historical destination for the trip, and eventually decided to visit Colonial Williamsburg in Virginia.

There seemed to be an abundance of timeshare-style apartment resorts in Williamsburg, along with two pancake houses on every corner, and not much else. We found a great deal at the Wyndham Kingsgate (where we could check in and out like a regular hotel) and drove in after work on Monday night. We had a two-bedroom unit for a few days and while we were definitely playing tourist more than we were there, it was really nice to have the little kitchen for leftovers and drinks, plus a big living room and porch to relax in at night before bed. Tuesday was our anniversary so after sleeping in with no alarm clock to wake us, we had lunch at a cute spot inspired by the Founding Fathers, Food for Thought, before heading back to the resort to check out the amenities. We didn’t feel like swimming but we checked out the arcade and played a round of mini-golf before we walked back to get ready for the evening.

Even though we have been a couple for five times as long as we’ve been married, we were really bad about taking photos together and have huge chunks of our relationship with either no photos together at all or only selfies to show for it. After getting anniversary photos last year and deciding to make a tradition of it, we wanted to find someone local to the Williamsburg area for our second anniversary. I went down an internet wormhole to find Meg of Meg Rose Photography on Instagram the week before our trip, and she luckily agreed to show us around Colonial Williamsburg while snapping some photos on Tuesday afternoon. Not only was she incredibly sweet and a talented unofficial tour guide, but the pictures she took are so special to us and I’m really happy we have these amazing memories in picture form to look back on.

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

 

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

Eric and Jess Pendergrass, copyright Meg Rose Photography

While we were walking around, Meg asked us where we were going to dinner. Eric told her the name of restaurant he had made reservations at, but admitted he wasn’t sold on the idea and would love any suggestions she had. She mentioned the local steak restaurant she and her husband went to for their second anniversary recently, Opus 9, and one quick internet search later – our reservations were changed. It was definitely the right choice and filled with little touches to make it memorable. We were feeling restless after the big meal and decided to play a few rounds of tennis on the resort courts before they closed at 10. When Eric was turning our rackets back in, he picked up a s’mores kit and we walked over to a nearby fit pit to curl up in front of before heading to bed.

Eric and Jess Pendergrass

We had coffee at the resort Wednesday morning before jumping in the car and driving to nearby Yorktown. Cue: the only time Eric has ever deemed it acceptable to listen to the Hamilton musical soundtrack all day – one of the best days of my life. The drive itself was through miles of beautiful protected wildlife, making it hard for us not to stop every two minutes at the scenic pullover areas. We parked on the beach and walked on the sand over to the Water Street Grille for lunch. After popping into a little dive bar on the walk back, we decided to head over to the Yorktown Battlefield for a history lesson.

Jess on a pebble beach

Yorktown beach and docks

Eric and Jess Pendergrass

We saw online that an old historical route tobacco farmers once used to transport crops to the port via shortcut was still there and supposed to make a nice walk. We found the entrance to the Tobacco Road Trail and it looked well maintained, so we took a risk and walked through the quiet woods for less than half an hour before finding the visitors center. If you like outdoor walking and ever visit Yorktown, you absolutely need to take this way to get there – it was so beautiful and peaceful. Learning more about the founding of our country was really humbling for us both, and we nerded out over the small museum exhibits. We walked around to several of the large monuments nearby and enjoyed the sunshine for a few hours with a bunch of retirees – it was great. We walked through Colonial YorkTown on the long way back to the beach.

Tobacco Road Trail Yorktown

Eric in Colonial Yorktown

Jess in Colonial Yorktown

It started to get chilly as the sun went down, so we took the nice drive back to Williamsburg and quickly changed for dinner. We found a bowling alley nearby and were really happy when they told us it was “free shoe night” because we are cheap, ha! Eric and I have opposite bowling styles; whereas Eric warms up over time and leaves the alley with more strikes as the night goes on, my game only ever goes downhill as my inferior arm strength gets the best of me. When he was consistently picking up spares and my total game score dropped pathetically into the 20s, we traded in our free shoes and headed out.

from where I stand: his and her bowling shoes

Williamsburg is a sleepy retirement city where we were constantly the youngest patrons in every establishment. That meant most of the town turned in for the night around 9, but we were still looking to have fun and found a couple bars open late, so we caught an Uber that way. We quickly realized that being open late in town didn’t equal being busy – besides a handful of college students from nearby William and Mary’s, we were the only ones still awake. The second bar we went to was having karaoke night, and we both initially looked at each other like “no way” when we walked in. It didn’t take long before we felt bad enough for the karaoke host being forced to do song after song himself that we agreed, “OK, I’ll do one if you do one.” With a receptive crowd of seven people total (including bartenders and the DJ), Eric and I both ended up singing a couple songs each and totally goofing around. After I gave the performance of a lifetime rapping Macklemore’s Thrift Shop, we figured it was time to call it a night and crossed our fingers until another Uber was within range to take us back to the resort.

karaoke night

We were checking out on Thursday but had our dog-sitter (Ollie’s best friend) booked until the evening so we could take our time on the way back. On the way out of town, we finally stopped at one of the many “world famous” pancake houses and the server let me order off the senior menu, “like a real Williamsburg resident.” It was definitely more low-key than anywhere else we’ve ever vacationed, but my husband constantly reminded me that anything can be fun with him.