A Scouted Weekend Getaway to Gloucester Main Street Village, Virginia

The Scout Guide Williamsburg and Chesapeake Bay, a scene of Gloucester Main Street Village

The towns of Williamsburg, Yorktown, and Jamestown, Virginia, are on most people’s radar as historic, colonial American towns. However, there’s another hidden gem nearby with roots in our country’s founding, that’s a vibrant, working village today. Gloucester Main Street Village is rich in history (Revolutionary War patriots mustered on the courthouse steps) and culture, with plenty of opportunities to enjoy incredible cuisine and a myriad of shopping options. Come along as we recommend everything you need for a weekend getaway to Gloucester Main Street Village, Virginia—from the best place for your morning caffeine fix to the ideal spot to grab a nightcap as you discuss your day living like a local.


When to Visit


weekend getaway to Gloucester Main Street Village
Gloucester Village. Photography by Sara Harris Photography.

Every June, Gloucester Main Street comes alive with the Gloucester Arts Festival. Throughout the month, guests can watch as plein air artists from across the country paint the Heart of the River collection, meet the artists during the Brews, Brine & Wine event at historic Timberneck Farm, see Main Street taken over by artists at Paint Main, enjoy the Virginia Symphony Under the Stars, Cocktails in the Garden at Goshen Farm, and instant favorite, Village Arts Day, which features a full day of performances and a bespoke artisan market.

June

SPRING


Stay


The Inn at Warner Hall, the ideal hotel for a weekend getaway to Gloucester Main Street Village
The Inn at Warner Hall. Photography by Jumping Rocks Inc.

Inn at Warner Hall. Located on 38 stunning acres, this waterfront plantation at the head of the Severn River, was established in 1642 by George Washington’s great-great grandfather. Today, the historic manor house has been completely restored, along with its numerous outbuildings, including brick stables, a dairy barn, and smokehouse to provide a glimpse of the past.

Also consider: Airbnb listings in the heart of Main Street like The Loft of Main Street, Bee Goode House, and Bitt of Home


Coffee


Sweet Tooth Cafe in Gloucester Main Street Village
Sweet Tooth Cafe. Photography by Sara Harris Photography.

Sweet Tooth Café. Start your Saturday on your weekend getaway to Gloucester Main Street Village with your morning cup of java at Sweet Tooth Café. You can take your pick between gourmet coffee and a variety of lattes. Sweet Tooth is also a full bakery and café boasting an expansive breakfast, lunch, and sweets menu.


LUNCH


Olivia's in the Village, the ideal location for dinner on a weekend getaway to Gloucester Main Street Village
Olivia’s in the Village. Photography by Sara Harris Photography.

Olivia’s in the Village. This Gloucester staple has been a part of the community for years, cementing itself as a go-to for locals. Olivia’s is a family centered, family-style eatery, open for breakfast, lunch, and dinner. Offering giant family trays, a vast menu, and river-focused appetizers.

Also consider: Patriots Grill, Bangkok Noi


AFTERNOON DRINK


Gloucester Brewing Co. in  Gloucester Main Street Village
Gloucester Brewing Co. Photography by Sara Harris Photography.

Gloucester Brewing Company. A weekend getaway to Gloucester Main Street Village wouldn’t be complete without a stop for a pint and good cheer at the village’s first micro brewery. Right on the corner of Main Street, the brewery is within walking distance of all the restaurants and shops of Main Street. Insider tip: Head up to the rooftop seating for incredible views.

Also consider: Kelsick Specialty Market


DINNER


 Lulu Birds Kitchen Gloucester Main Street Village
Lulu Birds Kitchen. Photography by Sara Harris Photography.

Lulu Birds Kitchen. This is the spot for elevated Southern comfort food. With reimagined traditional dishes and delicious drinks, Lulu Birds is an unforgettable restaurant experience.

Also consider: Farmasea (and try their Sunday brunch)


DO


Fine Arts Museum of Gloucester
Fine Arts Museum of Gloucester. Photography by Sara Harris Photography.

Take a walk back in time as you meander through Historic Gloucester. Experience the Gloucester Courthouse, built in 1766, other historic buildings and landmarks. True history buffs won’t want to miss the Gloucester History Museum, housed the historic Botetourt Building, which served as a pre-Revolutionary tavern. Art lovers will enjoy Main Street with not only art galleries to peruse (Gloucester Arts on Main, York & Main, Village Art Colony), a museum (Fine Arts Museum of Gloucester), but also the five colorful murals adorning the facades of buildings. Pro tip: The murals were made for Instagrammable moments.


SHOP


The Silver Box in Gloucester Main Street Village
The Silver Box and Up South. Photography by Sara Harris Photography.

The Silver Box. Specializing in women’s jewelry, clothing, accessories, and gifts, this local gem features popular brands like Simply Southern, Jack Rogers, and Brighton.

Also consider: Main Street is home to many boutiques, art galleries, antique shops, and a produce market. Take a leisurely stroll and enjoy popping in and out of these unique local businesses.


What to pack


Woman wearing a sleeveless dress with a vibrant blue and pink marine-inspired pattern, featuring seashells and starfish, showcasing a summer look for The Scout Guide.

ROBIN DRESS

Opt for a chic sundress while you pop in and out of the shops, like this one that nods to the area’s Chesapeake Bay location.

A classic white canvas sneaker with a minimalist design, featuring a lace-up front and a small logo on the side, positioned against a plain background, capturing the essence of The Scout Guide's simple yet chic aesthetics.

TAO’S SHOES

You don’t want your feet to wear out before you do. A pair of cute sneakers are the best choice when checking out this walking-centric town.

A smiling woman wearing a pastel-striped, hooded sweater paired with casual blue jeans embodies the relaxed yet stylish aesthetic of The Scout Guide.

BAJA HOODIE

When the temperature dips this fun outer layer is perfect for throwing over a tee. Pair with jeans and you’re ready to go.

On your weekend getaway to Gloucester Main Street Village, Virginia, one of the nation’s oldest living villages, comfort is key. Whether that’s with a stylish hoodie and jeans or a sundress, the right choice for shoes is always fashion sneakers. And of course, adding a little bit of bling elevates every outfit.


Know Before You Go


An artist in a straw hat and orange shirt is painting a scenic street view on a canvas outdoors, capturing the essence of the location in the spirit of The Scout Guide's local explorations.
Photography by Sara Harris Photography.

If you are visiting in June for the Gloucester Arts Festival, which is highly encouraged, make sure to check out the events calendar and book tickets in advance. It’s a busy time of year, so dinner reservations at the local hot-spots are recommended.


Insider Guides


Eager for more guidance for your Gloucester Main Street Getaway? Peruse the Insider Guides for The Scout Guide Williamsburg & The Chesapeake Bay: The Best Places to Stay in Williamsburg & The Chesapeake Bay, The Best Places to Shop in Williamsburg & The Chesapeake Bay, and The Best Places to Eat in Williamsburg & The Chesapeake Bay.

Follow The Scout Guide Williamsburg & The Chesapeake Bay editor/owner Sarah Harris at thescoutguide.com/williamsburg to discover what to do and where to stay, shop, and dine while on your weekend getaway in Gloucester Main Street, Virginia, and the surrounding areas. Businesses in bold are members of The Scout Williamsburg & The Chesapeake Bay.

Feature photo: Gloucester Village. Photography by Sara Harris Photography.