5. DoG Street Pub

This unpretentious gastropub offers a historic, casual setting perfect for a first (or 20th) date. Transformed and located inside an 80-year-old bank, share classic food with a British twist, like Shepherd’s Pie, Roasted Chicken, and Bangs & Mash with your loved one. Cozy up together in its warm atmosphere, complete with original marble floors and a skylight, and split a slice of Apple Pie for dessert.

4. La Piazza

From intimate booths to al fresco tables under the pergola, dinner at La Piazza will give you the perfect romantic evening with a taste of Italy! Modeled after a modern Italian bistro, the focal point of this casually elegant establishment is the fantastic food and hand-crafted cocktails. Share an Antipasto Board or delight in their traditional Italian pasta dishes with your significant other. Whether you’re joining them for their Tuesday Endless Pasta Night or their Saturday Happy Hour, this Merchants Square restaurant will be pleased to welcome you in.

3. Blue Talon Bistro

A bustling bistro, the Blue Talon offers breakfast, all-day, and weekend brunch menus so you can enjoy a date meal any time of day. Filled with traditional French cuisine, this laid-back eatery is a great place to enjoy a casual date or fancy enough to celebrate a relationship milestone. With menu items like braided pasta with mushrooms, classic Steak Diane, and blackened salmon, there’s plenty of choices for even the pickiest eaters. Make sure to save room for dessert, as they offer a classic crème brûlée and a traditional chocolate mousse that will be sure to please both you and your partner. Reservations are recommended for evening meals.

2. Berret’s Seafood

Since 1983, Berret’s Seafood Restaurant has offered some of the best regional seafood and produce around. Offering local favorites like the Sauteed Backfin Crabcakes, herb-crusted Mahi Mahi, and crispy crab puffs, as well as an oyster bar, there’s something for every seafood lover at the mainstay Merchants Square restaurant. Enjoy live music outdoors every night from 3:30 until 6:30pm or spend some more intimate time indoors and relax with your loved one. Reservations are recommended for indoor dining.

1. Fat Canary

One of the best places for a date night in Merchants Square is the Fat Canary. Located on Duke of Gloucester Street, this upscale restaurant has been a recipient of the AAA Four Diamond Award each year since opening in 2003. Boasting a seasonal menu that changes regularly, diners can look forward to items like Pan Seared Sea Scallops, Braised Beef Short Rib, and desserts like profiteroles and decadent cheese plates. Fat Canary is the perfect option when celebrating an anniversary or when wanting to celebrate something special with your significant other. In addition to their menu, Fat Canary also offers a wide selection of high-quality, unique wines and cocktails. Reservations for Fat Canary are required.

Located just steps from Colonial Williamsburg’s Historic Area, Merchants Square offers a variety of dining options. From fine dining, to family-friendly, to quick grab and go options, you’ll find something to suit every taste in the heart of downtown Williamsburg.