With so much history to discover, great food, and outdoor adventures in the Williamsburg area, it can be tricky to squeeze everything into one getaway. But planning by “hub” means travelers can experience more bucket list fun by focusing on one or two neighborhoods at a time. Here are some ideas about how to map out a vacation before checking out The WilliamsBLOG for more details about the region’s other abundant activities and restaurants. 


Wandering Williamsburg, from classic to contemporary


Merchants Square

Traveling back in time has never been so easy in this uber-walkable neighborhood in the heart of Williamsburg. Just a hop, skip, and a jump from the country’s largest outdoor living history museum, Colonial Williamsburg, the darling shopping district offers up unique souvenirs and experiences that can’t be found anywhere else. Outfit yourself in tartan at Scotland House, pick up new home decor at Brick & Vine, or add some shimmer and glimmer to your wardrobe at independent jewelry store Penny and a Sixpence before grabbing a bite or a brew.  Precarious Beer Project and Williamsburg Winery Tasting Room & Bar in the center of the Square means there’s no need to call for an Uber, while The Cheese Shop and the adjacent fine-dining restaurant Fat Canary invite you to indulge your urge to splurge. You can even hit the links at Golden Horseshoe Golf Club, which is just a chip away from the square. 

Merchants Square Shops


The Edge District

Foodies unite here with some of the area’s most tempting tastes. Follow your nose from savory meats coming off the smoker at Old City Barbeque, then head to 8 Shires Coloniale Distillery, Copper Fox Distillery, or Virginia Beer Co. for a refreshing tipple. In the mood to hang out? Shoot the breeze and feel the breeze at Casa Pearl, a former gas station transformed into an oyster bar and taco joint with contemporary roll-up garage doors that are open when the weather’s nice. 



New Town

In the mood for a Sunday Funday? Start with an epic all-you-can-eat brunch at Opus 9 Steakhouse before getting hands-on with some throwing competition at Axe Republic, or show off your billiards bravado at The Corner Pocket


Williamsburg Premium Outlets

Save some room in your suitcase for the amazing deals at the 135 stores at Williamsburg Premium Outlets, well worth an afternoon stroll. 


Midtown Row

Although Williamsburg is one of the nation’s most historic areas, there’s always something new and exciting. This includes Midtown Row, a collection of dining, shopping, and entertainment spots adjacent to the William & Mary Campus. Check out ethically made and sourced home goods and apparel at made, or trendy fashions for all sizes and budgets at House of Seven boutique. Adventurers can rent bikes or e-bikes for a few hours or a few days from Pedego (which also offers a bike delivery service). Foodies can spice it up at Amiraj, an Indian restaurant known for its curries and kebabs, or try other global fare in the form of Italian at Sal’s by Victor for pizza and pasta. 

Midtown Mural


Yummy Yorktown, for adventurers and history lovers



Whether you’re a power walker or a casual stroller, Yorktown's mile-long pedestrian Riverwalk offers plenty to see and do. From there, Yorktown Beach and fishing pier is easily accessible for swimming and sunbathing, while the more adventurous can rent a kayak or paddleboard at Patriot Tours and Provisions. Work up an appetite before heading to the boutiques and bistros at Riverwalk Landing for seafood at Water Street Grille or Umi Sushi. If you hit up the area on Saturday mornings, you’re also likely to find Market Days most months of the year. The weekly farmers pavilion features fresh flowers, produce, baked goods, music and art – and hands-on activities for the kids. For those who finished their vacay read early (or want to pick up an extra just in case!), there’s Yorktown Bookshop. The family-owned shop has a neat niche, offering a large selection of illustrated colonial history books for younger children. 

Yorktwon LOVEYorktown Sailboat


Main Street

There are few Main Streets in America largely protected by the National Parks Service, and Yorktown’s is one of them. Start your explorations at Yorktown Battlefield, where British forces surrendered to armies led by George Washington. You can join a park Ranger for a guided walking tour of the battlefield and 18th-century town, which includes the Nelson House, home to one of the most influential signers of the Declaration of Independence, and the Yorktown Victory Monument. 

Long before there was cold brew, espresso, or even ice cubes for summertime java, there was the Cole Digges House. Today, the 1726 home is home to Mobjack Coffee Roasters, and it’s the perfect place to power up during a day of explorations. If you’re looking for a low-key bite or quick pastry, this is the place in the heart of Historic Yorktown. Night owls may even want to grab a coffee later in the day to stay alert for the Yorktown Candlelight Ghost Tour, featuring the historic region’s highlights sans lights but with all the frights.  

Mobjack Bay Coffee - Hunter Hulbert Blog 


Around and About

Get a bit further afield (literally!) freely and easily thanks to the complimentary Yorktown Trolley. The ADA-accessible transportation takes visitors to nine of the region’s top destinations every 20 to 35 minutes most days of the year. 

Yorktown Trolley - Accessibility


Family-friendly Jamestown, something for all speeds and needs

From hiking to putting and thrills, ziplining, or rollercoastering, Jamestown offers something for everyone looking for a place to stay and play. 


Hit the green

At Kingsmill Resort, three golf courses and luxurious, family-friendly accommodations await. For tee time diehards, the Jamestown area is the best to hit the green at courses, including Colonial Heritage Golf Club, Kiskiack Golf Club, and Ford’s Colony Country Club

Golf -  Colonial Heritage


Outdoor adventures

Want to fly with the birds? Go Ape Zipline and Adventure Park provides the opportunity to do just that, with obstacle courses and suspended bridges providing thrills high atop tree canopies. Or, flock to Busch Gardens, where rollercoaster fans can check a few things off their bucket list. Among the 50 rides and attractions are Pantheon, the world’s fastest multi-launch roller coaster, and DarKoaster, North America's first all-indoor straddle coaster.

Griffon Roller Coaster at Busch Gardens


Parks and recreation

Hikers can make new tales on trails at any of the area’s many forested retreats. Freedom Park’s 600 acres include multi-use trails (including an ADA-accessible 1-mile paved stretch), and 20 miles of mountain bike trails. Freedom Park is also home to Williamsburg Botanical Garden, two lush green acres with herb plantings, a butterfly haven, and a cove with plants native to Virginia. Want to take a dip? Launch a bobber in the water fishing at Chickahominy Riverfront Park, or hit up the swimming pool and slide or adjacent splash pad. At Powhatan Creek Park and Blueway, it’s the best of both worlds, with views of colonial American landmarks like James River and Historic Jamestown – and sightings of protected birds like bald eagles.

Williamsburg Botanical Garden Freedom Park Trail

Long before the bald eagle was considered our nation’s symbol – and before the nation existed – there was the first permanent English colony. Visitors can learn more about them and Virginia’s Indian population at Jamestown Settlement while climbing aboard re-creations of the three sailing ships at James Fort.

Jamestown Settlement Ships