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Top 5 Desserts in Williamsburg, Virginia USA

Updated on February 23, 2016

Should you ever be in Williamsburg, Virginia, take it from a native of the area that the best desserts are easily found here. Being a complete chocoholic and fortunate enough to experience most of my dates (with my now husband) in Williamsburg, I got to know the dessert selection very well. While there are many fantastic desserts that did not make this list which are definitely worth tantalizing your taste buds over, let’s focus on the top 5 dessert indulgences.

1. Death By Chocolate

Sold at Trellis

403 W Duke of Gloucester St


The Trellis Bar and Grill

If you are visiting Colonial Williamsburg you are in the perfect spot to find the best dessert in all of Williamsburg. The famous “Death by Chocolate” is available at the restaurant Trellis in Merchants Square. It’s a lovely restaurant, but should you choose to only order dessert they are more than happy to oblige. However, as with most restaurants, if you are not ordering a meal and the dining room is crowded, they may request you sit at the bar. Not to worry, it’s an upscale establishment, no smoking, and the bar is even suited for kids. I’ve been in there when families have come in just for dessert, sat at the bar, and enjoyed their cake with nothing more than glasses of water.

As for the dessert, absolutely delicious doesn’t even begin to describe it. It is made of seven layers of differing chocolate. It really is chocolate overload, but for a true chocolate lover it isn’t overwhelming, it is happily satisfying. You may want to share this cake as its portion is perfectly suited for two.

2. Cookie Monster

Sold at Aromas

431 Prince George Street


Aromas Coffeehouse & Cafe

Also in Merchants Square, you will find a delightful little coffee shop a few streets away from Trellis. They have an assortment of desserts (and other menu items of course) but their top offering is the “Cookie Monster.” Two chocolate chip chocolate cookies sandwich a thick peanut butter ganache filling. It is scrumptious! It is also large and another good candidate for a shared dessert for two.

The problem is that this dessert is so delicious that it almost always sells out immediately. It is in stock usually every other Thursday. Time it just right and you may luck into this tasty wonder of Williamsburg.

3. Whitley’s Chocolate Covered Peanut Clusters

Sold at Whitley’s Peanut Factory

1351 Richmond Rd


Whitley's Peanut Factory

Virginia is known for the best peanuts anywhere. There are numerous Virginia peanut companies and I’ve tried most of them, but in my opinion Whitley’s peanuts are the best. Even better, their peanut dessert varieties are exceptional. The location of this shop is a bit out of the way. It’s a few miles from Colonial Williamsburg and is found on Richmond Road (a main road for dining and shopping). It’s worth hunting down the quaint little shop. Sure, there are peanut shops in Merchants Square, but if you want the best go with Whitley’s.

I highly recommend getting the Chocolate Covered Peanut Clusters. Other tops favorites are the Peanut Fudge, Chocolate Peanut Delights, and White Chocolate Cashew Clusters. Best of all, should you not be able to visit Williamsburg, these delicious treats can be ordered online! Which makes me happy now that I live in Texas and nowhere near my beloved peanut shop.

4. Monster Apple

Sold at Rocky Mountain Chocolate Factory

5715-57 Richmond Road


Rocky Mountain Chocolate Factory

The most popular place for shopping in Williamsburg is Prime Outlets. After working up a chocolate craving thanks to all of the outlet bargain hunting, Rocky Mountain Chocolate Factory is perfectly located within the shopping center. They have the best caramel apples anywhere; the trick being they use green apples instead of red (sorry Wythe Candy in Merchants Square but a red apple doesn’t give that perfect balance of sweet and tart the way a green apple does). I recommend the “Monster Apple” which is coated in caramel, pecans, white chocolate, and milk chocolate.

Honorable Mention: Chocolate Dipped Frozen Banana with nuts
The frozen banana tastes like it should be banana ice cream but it’s really just a banana that has been frozen. Tastefully tricky!

Another advantage of Rocky Mountain Chocolate Factory is that their locations are not at all exclusive to Williamsburg, Virginia. They have stores across the US so you can look for a location near you.

5. Macadamia Nut Pie

Sold at Fat Canary

410 W Duke of Gloucester St


Fat Canary

Back to Merchants Square and right across the street from Trellis, number 5 on the list is surprisingly not a chocolate dessert. The Macadamia Nut Pie is similar to pecan pie but done better. In fact, I’m not a fan of pecan pie yet I love the Macadamia Nut Pie. Maybe it’s the difference in the nut flavors, maybe it’s the freshly made quality of this individual sized pie, and maybe it’s a secret recipe that Fat Canary is known for producing specialty items.

Honorable Mention: Chocolate Pyramid Cake
Delicious with incredible visual appeal but the Macadamia Nut Pie wins out on taste, but just barely.

One thing to note about Fat Canary, they change the dessert menu regularly. The Macadamia Nut Pie and the Chocolate Pyramid Cake were available as of Summer 2009 but could change. But should you be in Williamsburg you should stop by and find out what they have for dessert. And should you want to order dessert only, sit at the bar and be sure to ask for David, the best bartender ever. Even being gone for two years he still recognized my husband and I when we came in for dessert last summer. Granted, there probably aren’t many young couples that come in, sit at the bar, and only order dessert. But he likes us, it probably helps that we leave a decent tip. I recommend you do the same.

Should you ever be in Williamsburg, Virginia now you know where to find the best desserts in the area. We all know vacation is about letting go of the restrictions of everyday life and that includes eating plenty of dessert. Enjoy!


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