As the state slowly begins to open its doors again, Portsmouth is taking care and caution to safely welcome visitors back for much-needed getaway time. Only a short drive away for the majority of Virginians, Portsmouth is the perfect small town to explore, without the worry of big crowds. We’ve rounded up a whole weekend’s worth of activities to enjoy during a visit to stretch your legs, refresh your mind and rediscover what it means to take a vacation.

Portsmouth is a charming waterfront community in the center of Hampton Roads, Virginia, only 30-minutes from the oceanfront and less than an hour from Colonial Williamsburg.  In its heart is Olde Towne, a charming main street community where you’ll find brick sidewalks and antique lamp posts, independent shops and restaurants, and one of the largest collections of historically significant architecture on the east coast. Take in the local history, dine alfresco, enjoy a locally brewed craft beer, or, spend some time exploring nature by land or by sea. It’s a beautiful setting for a quiet getaway.


1. Explore the Olde Towne Historic District

Take a step back in time when you stroll the tree-lined streets of Olde Towne Portsmouth, Virginia. A variety of architectural styles span three centuries and include Georgian, Colonial, Federal, Gothic Revival, and more. A visit to Olde Towne features towering sycamore trees, brick sidewalks, beautifully restored homes, and monuments to past heroes. But more importantly, the Olde Towne Historic District is a compendium of American history.

There are two ways to explore the history and stories of Olde Towne. Pick up a brochure on the Path to History for a self-guided walking tour stretching from the Norfolk Naval Shipyard to the Portsmouth Naval Medical Center with a meandering walk through the Olde Towne neighborhood. The brochure includes facts and stories about places along the way and interpretative signage goes into greater detail at stops on the Path to History.

The other alternative to learn about the history of our city is to take a guided walking tour with Mary Veale and the Colonials.  Returning in July, this troupe of storied characters from Portsmouth’s past will guide you through the streets of Olde Towne while telling tales and singing songs about the life and times of the era. Private tours can be booked prior to your arrival or join them for a themed tour scheduled at various times.

And finally, no tour is complete without getting a peek inside one of these magnificent homes. The Hill House Museum is an English Basement home that contains artifacts from the Hill family acquired and maintained from the early 1800s through the late 1950s when the last of the Hill family moved away. The house is owned and operated by the Portsmouth Historical Society and is open Wednesdays and Saturdays for tours.



2. Dine Outdoors

Nothing says summer like dining alfresco. Portsmouth, especially Olde Towne, is known for its locally owned and operated restaurants and many of them offer outdoor dining. Choices include dining along the banks of the Elizabeth River with views of passing ships and a working harbor to secluded garden patios accented with flowers and plants. The sidewalk dining experience is a great way to people-watch while enjoying your meal. You can enjoy breakfast, lunch, and dinner in the great outdoors all within a short walk from local lodging. Check out the article called Outdoor Dining in Portsmouth Virginia for a list of some of the restaurants you might consider.



3. Play Outside

While Portsmouth is mostly a suburban destination, the city boasts several beautiful nature parks where you can enjoy fishing, golf, kayaking, hiking, and more. Fishing piers are open on the Elizabeth River at City Park, along with a 9-hole golf course and driving range for a little extra practice. This 93-acre park has beautiful gardens to explore and waterfront picnic shelters to enjoy spectacular views.

If you want to get out on the water, rent a kayak at Hoffler Creek Wildlife Preserve located on the northwestern edge of the city. This 142-acre preserve offers hiking, wildlife viewing, and kayak rentals to explore by water. Check the Hoffler Creek website for special programs and guided walks or paddles offered throughout the year.

Paradise Creek is another urban oasis park at the south end of the city. If you have your own kayak or canoe, you can put it in at the park. The park offers 2 miles of woodland trails along with 11 acres of tidal wetlands. Check the Paradise Creek website for programs and guided paddle opportunities. Don’t miss the wonderful art installations located throughout the park.

For the golfing enthusiast, Portsmouth has a Curtis Strange Signature, 18-hole, par 72 public course located in the center of the city. Bide-a-Wee Golf Course is open year-round and maintains a 4.4 rating on Google reviews.

When planning your trip, check out the article 10-Things to Do Outside in Portsmouth, Virginia to learn more about all of the parks or Bide-A-Wee Golf in Portsmouth, Virginia to learn more about playing golf while visiting the city.



4. Explore Local Shops

Shopkeepers in Portsmouth pride themselves on their independence and their hospitality. As you walk around Olde Towne, you find a variety of unexpected surprises, like an authentic German “markt,” a secret garden courtyard, or a pennyfarthing from the mid-1800s. Many of these shops have been open for more than 20 years while others are relatively new to Olde Towne. As you stroll along High Street, look for kitchen specialties, art galleries, home and garden items, apparel for men, women, and children, vintage treasures, toys, bikes, sweets, and much more. And on Saturdays, there’s even an authentic small-town farmer’s market to visit. For the real shopping enthusiast, take a drive out to Churchland or Midtown and discover other small businesses offering a variety of trinkets you can’t live without. Find a partial list of shops under Where to Shop on our website.



5. Walk (or Bike) Your Art Out

The Portsmouth Art and Cultural District, located in Olde Towne, features over 20 works of public art, including murals, sculptures, museums, and monuments. This collection can be found on the sides of buildings, on street corners, inside pocket parks in the Olde Towne neighborhood, even on the sides of electrical boxes. You can explore on your own or take a scavenger hunt with clues to find certain pieces of the collection. Check out the article, Walk Your Art Out to learn more and download your scavenger hunt tracking form. On the second Saturday of each month, bring your bike and Bike the Arts with a tour guide to tell you about each piece on the tour. Touring the public art is a great way to get exercise, on foot or by bike, and a fun way to explore the creativity of local artists.



6. Check out Breweries

After a full day of play in Portsmouth, settle in for a cold, refreshing brew. Portsmouth is home to two breweries. MoMac Brewing Company, named for the famed clash of the ironclads Monitor and Merrimack, is located in Churchland, about a ten-minute drive (or Uber) from Olde Towne. Brewed on-site, MoMac beer includes standard lagers, stouts, and IPAs, along with a dynamic list of specialty beers for customers to enjoy.  There is often food trucks and live music found at MoMac.  Enjoy the beers inside or on the patio.  Back down in Olde Towne, look for Legend Brewing Depot located at High Street Landing on the Elizabeth River. Home-based in Richmond, Virginia, Legend Brewing opened its first satellite location here in Portsmouth in 2018. They serve standard and specialty beers brewed in Richmond along with an exclusive selection brewed on-site in Portsmouth. With a full service bar and restaurant, guests enjoy dining outside with views of the river or inside the rotunda looking out over the water.

For the true beer lover, check out some of the other pubs around town that offer these local beers along with a large selection of imports. The Bier Garden has over 400 imported beers from Europe and about twenty taps while Humboldt Steel, Gosport Tavern, and Roger Brown’s have over twenty beers on tap. It’s a great way to wind down your day.



Make It a Weekend

Spend the weekend overlooking the Elizabeth River at the Renaissance Portsmouth – Norfolk Waterfront Hotel or, if you’re traveling on a budget, at the Quality Inn and Suites Olde Towne. Both properties are within walking distance of bars, restaurants, shops, and historic sites. Rest easy knowing these properties are being maintained with the best safety standards as set forth by Marriott and Choice Hotels. These measures include disinfecting each room upon checkout, limiting service to meet individual guest needs, and wiping down doorknobs, elevator buttons, and other high traffic, high touch surfaces. Face masks are required in all public areas for your safety and the safety of staff.

The Renaissance Hotel is located along the North Landing with spectacular views of the working harbor. The rooms were renovated in 2019 and early 2020 with new fixtures, baths, and bedding. It provides a local vibe and modern style. This upscale property is highly rated and known for its friendly staff and quality service.

The Quality Inn Olde Towne is located at the western entrance to the Olde Towne Historic neighborhood. A short stroll to the east puts you into the heart of the neighborhood and down to the waterfront. Or head south a few blocks to High Street, the Olde Towne commercial district to enjoy the shops, bars, and restaurants. The Quality Inn is a budget-friendly, limited-service property with breakfast included each morning.

Remember, pools and fitness centers are closed for the time being but will re-open as soon as it is deemed safe to do so.  For a list of available lodging, visit the Where to Stay section of our website.