48 Hours in Williamsburg, VA


J and I went to Williamsburg this past weekend with one of our fav couples, and the historic town did not disappoint! I’ve always wanted to visit, thanks in part to Felicity and the American Girl series (#tbt), and of course wanted to take advantage of it being an easy drive from DC.

We got to Williamsburg around at around 2pm on Saturday, checked into the hotel, and headed to Williamsburg Winery for wine + snacks before freshening up before dinner. Sunday was filled with more food, history, and lots of walking…pretty much what you’d expect a Williamsburg weekend to look like. Breaking down what we did (and where we ate, of course) below!

Williamsburg, VA

Williamsburg Winery: We stopped by the winery Saturday afternoon and it was packed! Probably since it was 70 degrees and everyone had the same idea. It’s really easy to get to (read: a short drive from town) and the wine was really good and bottles reasonably priced. We opted for a table at the restaurant and got a meat + cheese board + the boys got tastings and K and I split a bottle of rosé…because it was definitely rosé weather. Highly recommend if you’re in the area!

Blue Talon Bistro

Blue Talon Bistro: This came highly recommended and did not disappoint! They have a boneless short rib special on Saturday night so the boys got that, and the girls both got the chicken and mushroom crepes. Everything was so good, including the cocktails (I had the Blood & Sand) and the dessert–omg. The best chocolate mousse. If they ask if you’d like more, just trust me and say “yes please” or “keep it coming” :)

Food for Thought: Our hotel was right across the street and this felt like the most random spot, but it’s rated over 4 stars on Yelp and we decided to try it out for a quick breakfast on Sunday morning. There was a 25 minute wait for a table (for four people) at 9:30am, so we opted for immediate bar seating. They give you a complimentary basket of beignets, which was great, and the breakfast menu is filled with unique twists on classics; for instance, benedicts made with crumpets instead of English muffins, and fried grit fritters with gravy. Everything was good but quite heavy–it’ll tide you over for a few hours.

Williamsburg, VA

L.L. Bean shirt (c/o; size down) – Rag & Bone jeans (old) – Corso Como flats via Tuckernuck (old)Longchamp tote (this fits so much stuff!)Warby Parker sunnies

Paul’s Deli: A college bar that serves good food + cheap drinks (hi, $12 pitcher of delicious local beer)–I had a grilled cheese and fries and others had fish + chips, spaghetti, and a hefty sub. All of us left very full and happy…everything is inexpensive and great. Highly recommend for a casual lunch!

The Trellis: They’re known for great drinks and their “Death by Chocolate” cake–we went for dinner on Sunday but were so full from the rest of the day that we all got salads or soups and didn’t even try the specialty cocktails. I obviously couldn’t pass up the chocolate cake, though, and let’s just say you’ll want to make it a priority! The Trellis is located in the main part of Merchant Square and is an easy walk to Blue Talon and lots of other restaurants + shops.

Casual look

Jamestown Settlement: America’s first permanent English colony is definitely worth visiting–it offers a good dose of history, of course, plus beautiful views and is just a short drive from Williamsburg. We spent about two hours there…I’d pack comfortable shoes and some sunscreen if it’s warm out! Personally, we’re glad we did this over Colonial Williamsburg (mentioned below), as it was less interactive and more unstructured, in a good way. Also, being next to the water doesn’t hurt :) Tickets to access the whole grounds are $14.

Jamestown Settlement

Colonial Williamsburg

Colonial Williamsburg: There’s a whole historic Colonial Williamsburg area that you can walk around without a ticket…the first part is Merchant Square, which has all the restaurants and shops (Blue Talon and The Trellis, as mentioned earlier, plus The Peanut Shop–SO good, lots of samples, and fun gifts to take home, and The Cheese Shop–supposed to be great for lunch but is fun to window shop, too). Right next to Merchant Square is the interactive part of Colonial Williamsburg that requires a ticket…you stop in and out of historic homes and talk to reenactors about various aspects of colonial life.

Williamsburg, VA

Colonial Williamsburg

Colonial Williamsburg


  1. 1

    I’ve always wanted to visit Williamsburg, too! (Loved Felicity, LOL.) Looks like a great spot for a long weekend.

  2. 3

    I love Williamsburg! I actually go every year and while I’ve heard a lot about that death by chocolate I’ve never had it… I’ll have to correct that during my next visit.

  3. 5

    What a fun getaway! I visited Williamsburg years ago with my family, but I’m definitely overdue for a trip back!

    • 6

      Everyone seems to have made a family trip there at some point or another! (or a school trip) – getting to try all the food + drinks as an adult would definitely be a highlight :)

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