Experience the best of the best with this Top 8 list of things to do and see in Portsmouth.
Walk through history and see Olde Towne’s origins and it’s continued evolution.
Plan for your visit and explore Portsmouth with the Visitor Directory.
Springtime is a lovely time to visit Portsmouth. The temperate climate along the Elizabeth River means early blooms along the tree-lined streets. The stately old homes are accented with forsythia, cherry blossoms, tulips, and other vibrant spring foliage. Ready to shake off the doldrums of winter, the town comes alive with a weekly farmers market, music and dining al fresco, historic re-enactments, festivals, outdoor recreation, boating, and so much more. Here are 10 things you can look forward to doing in Portsmouth, Virginia this spring.
Bike the Arts
Engage the British
Crash a Party
Grow Your Garden
Paddle in the Moonlight
See a Show
There are plenty of places around town to take a bike ride. You can pick up a Path to History brochure at the Visitor’s Center and take a ride through three centuries of history and some pretty fabulous architecture in Olde Towne. You can take a ride through nature at Paradise Creek Nature Park. Ride out to Shea Terrace and have lunch at Dock of the Bay on Scott’s Creek. Or, use your bike to explore the Portsmouth Cultural Arts District.
The Portsmouth Cultural Arts District is centered on and around High Street in Olde Towne, with a developing extension up to Elm Avenue. It includes over a dozen murals, sculptures, and painted boxes. While you can ride or walk the tour on your own by accessing the map on the website, it’s a lot more fun to take a free guided tour on the Second Saturday of the Month. Tours depart from High Street Landing at Legend Brewing Depot at 10:30 a.m. Be sure to check out the outdoor sculpture exhibit at the Portsmouth Art Center and the Faculty Show at the TCC Visual Arts Center. Insiders Tip: If you need to rent a bike, try an electric bike from Pedigo Norfolk….just take the ferry to get it. A limited number of Pedigo Electric bikes will be available in Portsmouth starting in June. Also, don’t forget to check out Classic Cycles on High Street to see new and vintage bikes.
The Portsmouth Art and Cultural Center will host two re-enactment events this spring. The first event, A Post Such As Portsmouth, takes place March 28 and 29. Guests step back in time to see what life was like on the streets of Portsmouth when General Benedict Arnold and his soldiers occupied Portsmouth in 1781. Characters include members of the Royal Navy and other military, as well as civilians, some loyal to the Crown and others who support the Patriots in the quest for freedom. Emotions are high and duplicity reigns. See the action unfold in vignettes staged throughout the day, performed by about a hundred re-enactors from far and wide. For more background and a schedule of vignettes, refer to the article “A Post Such As Portsmouth – 1781.”
On June 20, there is another opportunity to engage the British at a re-enactment called “A Laudable Zeal: The Battle of Craney Island.” The Battle of Craney Island was a significant defeat for the British on June 22, 1813. The event is produced by Fort Norfolk & Frigate Constellation, 1812, a dynamic living history unit that strives to research, interpret and reenact the War of 1812 in the Chesapeake region. The re-enactment includes first person portrayals of Royal Navy sailors, along with American military and civilian personnel. This living history event starts at 9 a.m. and goes until 4 p.m. at the Portsmouth Arts and Cultural Center, High and Court Streets.
Portsmouth, Virginia can trace its history back to 1608 when Captain John Smith explored the waters of the Elizabeth River and determined that with the deep water channels and the natural hardwoods, this area would be ideal for shipbuilding. Settlement began later and the entire area was known as Norfolk County. In 1752, Colonel William Crawford laid out a plot of land to accommodate business and residential and the town of Portsmouth was founded. Walking through the tree-lined streets of Olde Towne reveals a variety of architectural styles consistent with the time they were built. Take a drive through Park View, Port Norfolk, Cradock, or Truxton and discover Portsmouth’s other nationally registered historic districts to see architecture from the late 1800s through planned neighborhoods for shipyard workers during WWI.
The most popular way to explore Portsmouth’s rich history is a self-guided walk along the Path to History. The path connects Fort Nelson Park at the Portsmouth Naval Hospital through the Olde Towne residential and business neighborhoods to Gosport Park at the Norfolk Naval Shipyard. Interpretive signage and monuments detail famous events and people associated with Portsmouth throughout history such as Lord Dunmore, General Cornwallis, Benedict Arnold, Andrew Jackson, Billy Flora, the Underground Railroad, Yellow Fever Epidemic, and so much more. Along the way, many people encounter Mary Veale and the Colonials, a troupe of talented actors who bring history to life. They regularly stroll the streets of Olde Towne to entertain and educate visitors and locals alike. Private tours and specially-themed tours are also offered by Mary Veale and her cadre of characters.
Steeple to Steeple Tour
Other ways to explore history include taking part in the annual Steeple to Steeple tour of Portsmouth’s historic churches on May 9th. During the event, churches dating back to 1762 open their doors and docents point out Tiffany windows and other treasures while describing the important role each church played in history. The Hill House Museum allows visitor to take a look inside one of olde Towne’s historic homes and see how one family lived through multiple generations in the structure. Don’t miss the Mother’s Day High Tea on May 9th. For a look at maritime history, don’t miss the Portsmouth Naval Shipyard Museum and the Lightship Portsmouth. Learn more about Black History during segregation at the Portsmouth Colored Community Library Museum, Jewish History at the Jewish Museum and Cultural Center, and the important part rail transportation played in Portsmouth at the Railroad Museum of Virginia.
So much history keeps history lovers involved, engaged, and coming back year after year. Virginia IS for history lovers.
Getting outside is the natural thing to do in spring. So why not attend a party, right? Portsmouth is known for throwing some great street parties and festivals. Here’s some exciting events this spring:
First Fridays Concert Series -This free event features different artists each month. It takes place in the courtyard of the Portsmouth Art and Cultural Center from 5 p.m. until 8 p.m. on the first Friday of each month starting March 3 and ending October 2. Artists include Julie Clark, the Wampler Brothers, Less Cowbell, Push Comedy Club, Court Street Company, Brackish Water Jamboree, Lewis McGhee and others. Adult beverages available for sale courtesy of PortsEvents.
St. Patrick’s Day Street Festival – The Olde Towne Public House is closing the street and holding an old fashioned Irish throw down featuring three bands and a night time DJ, Irish fiddlers and some bagpipers, crafts and glass blowing, a corn hole tournament, bounce house for the kids, and of course food and drink specials all day long. The event stage is in front of the Olde Towne Public House at the corner of High and Court St. Pubs and Restaurants throughout Olde Towne will be offering food and drink specials as well.
Pub Crawl – Then on Tuesday, actually St. Patricks Day, there’s an Irish Pub Crawl featuring Momac Brewing and ten different pubs. The Crawl begins at 6 p.m. at Gosport Tavern and ends at 10 p.m. at Roger Browns. The Olde Towne Shuttle will be running if you need a ride. Free parking.
Get a complete run down on everything St. Paddy’s Day with a post called “Celebrate St. Paddy’s in Portsmouth”.
30th Annual Umoja Festival – Virginia’s longest running festival celebrating African-American Culture and Heritage kicks off Friday, May 22 at 5pm with opening ceremonies followed by 4 bands. On Saturday at noon, the festival opens and features 5 bands throughout the day, a children’s area, and heritage stage featuring theatrical performances by Frederick Douglass, Billy Flora, James Armistead Lafayette, Martha Ann Fields, and Coretta Scott King. That evening, there’s a special (paid) concert at the Atlantic Union Bank Pavilion. On Sunday, the Heritage stage continues but the music shifts to traditional and progressive gospel performances. There are food, craft, and apparel venders throughout the weekend. Parking is free. The event is located at the festival field adjacent to the Atlantic Union Bank Pavilion.
43rd Annual Seawall Festival – Talk about a party with some legs! This party has been happening to coincide with Norfolk’s Harborfest since 1977. This year, the party starts Friday night after work. It takes place at High Street Landing. The party goes from 6 p.m. until 11 p.m. and features Island Boy, Strictly Business, and the Original Rhondels. On Saturday, the music starts at 2 p.m. and ends at 9:15, just before the big fireworks show over the Elizabeth River. Bands performing include Champagne Band, Hotcakes, Blaque Velvet, Soul Intent, RaJazz, plus one more to close the show. Adult beverages and children’s activities are both available. Free parking, free docking.
Sunset Thursdays on the Water – A weekly street party with music and adult beverages, Sunset Thursdays take place at High Street Landing and features a different band each week. Jazz, Beach, Reggae, Rock, Country, Blues, Motown, and Funk, each band has a different sound.
The party kicks off on Thursday, June 11th and runs through Thursday, September 3rd, from 6:30 p.m. to 9 p.m. Bring your lawn chairs and kick back and watch the show or get up and dance when the mood strikes. Grab some dinner at a local restaurant or get something from one of the food trucks on site. Free parking and free docking.
The Race to Cock Island – Cock Island is one of the historic nicknames for Portsmouth (or someplace nearby). The Race is a sailing regatta on the Elizabeth River and sailing vessels come from all over the Mid-Atlantic to compete. What’s a sailing regatta without a party to go with it? The event takes place Saturday, June 13th. The race kicks off in the morning with spectators lining the seawall to watch the boats depart. That evening, at 5 p.m. at High Street Landing, the band Hotcakes takes the stage for an after-race party. The party is open to the public. Adult beverages available, Free parking.
On the first Saturday of every month, the Olde Towne Antique and Flea Market sets up in the County Street Parking Garage and offers a huge variety or collectables, vinyl albums, antiques, toys, jewelry, furniture, art work and much more. Depending on the month, there are usually 60-70 venders each month.
Just around the corner, look for Village Thrift Olde Towne, located at 309 High Street. They offer a variety of high-end quality clothing, some haute couture and some vintage. They also have furniture, wall hangings, silver, and a lot more in their 10,000 sq. ft. showroom. What makes Village Thrift Olde Towne truly special is that they employ differently-abled individuals at fair wages in an effort to give back to the community. It’s easy to recognize Village Thrift by their distinctive and beautifully designed window displays.
Continue up High Street and be sure to stop into Cycle Classics at 427 High Street and look at a few of the vintage bikes. Cycle Classics is a shop that specializes in a wide variety of new and retro bikes, restorations, refinishing, frame upgrades and repairs, and superior mechanical work, including custom frame building. Be sure to speak with Gordon, the owner, he loves to talk about the vintage bikes.
The quest for treasure doesn’t stop there. At the corner of Washington and High Street, look for Way Back Yonder Antiques. An Olde Towne business for more than twenty years, Way Back Yonder offers a general line of quality items including period furniture, lighting, accessories, china, porcelains, pottery, textiles, estate jewelry, coins, collectibles, metalwares, glassware, crystal, estate and sterling silver flatware and hollowware. Their selection of antique and estate silver is the largest in eastern Virginia.
Thrift stores and other vintage item places are not limited to Olde Towne. Check out Cottage Thrift on Victory Boulevard, Port City Thrift on Portsmouth Boulevard, and the Goodwill has a large store on High Street in Midtown. Take a ride down George Washington Highway or out to Churchland and discover new places to hunt for treasure. It’s springtime, so look out for neighborhood yard sales as you ride around.
When planning your garden, your first stop must be Anderson Wright Rooms and Gardens at 622 High Street. Set around an enclosed courtyard, Anderson-Wright Rooms & Gardens offers an extensive selection of decorative home and garden furnishings including cast iron urns, cast stone containers and statuary, as well as cast iron and aluminum furnishings. Their courtyard is an amazing place to inspire your next garden or patio project. Anderson-Wright also offers a collection of 18th and 19th century architectural windows and doors from India and European countries.
With a plan in place, it’s now time to pick your plants. The spring offers a number of plant sales, too. On April 24-26, historic St.John’s Episcopal Church presents the St. Fiacre Flower Festival. It kicks off Friday evening with a reception and early bird sale fundraiser for charity and then on Saturday and Sunday, it’s free to the public to stop by and shop for plants, flowers, baked goods, and more.
The Virginia Cooperative Extension, located at 105 Utah Street in Midtown has two plant sale events. The first is the Early Bird Greenhouse Plant Sale on Saturday, April 11, from 10 a.m. – noon. They have an Open Garden Event on Saturday May 2 that includes free gardening lectures, a plant sale, garden tours and more. Gardening classes are both fun and rewarding. Over at Paradise Creek Nature Park, they are offering a class on Native Medicinal Plants, how to plant them and use them, on May 9 and then on June 27, they have a special workshop on Growing Native Plants from Seeds.
Norfolk County Feed and Seed, located at 1110 Airline Boulevard in Midtown, has been a Portsmouth institution since 1947. With a friendly, helpful staff, the store is proud of it’s heritage in Portsmouth and even displays some of the original items used when it began over 70 years ago. It’s an old-fashioned general store in the heart of the city and has some of the best plants available throughout the region, one of the largest selections of seeds for growing vegetables and flowering plants, along with household items, decorative lawn and garden items, cookware, pet supplies, and so much more. When they say ‘general store,” they mean it. Don’t miss the opportunity to explore a small piece of Portsmouth’s agrarian roots in truck farming, the practice of raising vegetables for barter which can be traced back to 1784.
At the top of the “Not to Miss” list when “Growing Your Garden” while in Portsmouth is Virginia Historic Garden Week’s Portsmouth Home and Garden Tour. It’s an opportunity to celebrate the 100th year of Virginia’s Historic Garden Week, “America’s largest open house” when over 250 homes are opened for tours across the Commonwealth. Portsmouth is fortunate to be included again in 2020. The Portsmouth Home and Garden Tour takes place on Saturday, April 18th. Check in is at the Portsmouth Art and Cultural Center and then the tour is self guided afterward. It includes five historic Olde Towne homes and gardens plus the Hill House Museum. Tickets are $40 and may be purchased online or on the day of the tour.
Feel young again this year as the Children’s Museum of Virginia, the largest of it’s kind in the state. The museum celebrates forty years of educating and entertaining kids and adults from all over the world. In addition to all of the planned exhibits and events for children, there is a very special night happening on April 30th called Adults Night Out: Framed Into Art. From 5:30 p.m. until 8 p.m., adults are invited to embrace their inner child at an adults-only night of artistic fun on Thursday, April 30th from 5:30pm – 8:00 pm. Experience Framed: Step Into Art and all of the wonderful exhibits at the Children’s Museum of Virginia child-free! There will be a special art-focused planetarium show, and guests will be able to get their likeness drawn by caricaturists. Drinks and light refreshments will be served. Tickets are $15 for non museum members.
As part of the 40th Anniversary celebration, there will be special exhibits, planetarium shows, family-friendly events, and discounted admissions offered throughout the year. Families who have visited the museum are encouraged to share memories and photos on the Children’s Museum Facebook page. Programs and details will roll out in the coming months, but more information can be found in a related article called “The Children’s Museum Celebrates.”
Portsmouth Sweet is a new dessert trail across the city. It includes specialty desserts from eleven different restaurants as well as specialty items from two hometown bakeries. Portsmouth is known for its independently owned and operated restaurants, mom and pops run by chefs and local owners. Together, these restaurants offer a diversity of quality foods on par with restaurants around the world. The trail showcases a variety of desserts from cupcakes and pies to vegan and gluten-free options. Did you know frosting could be made from avocados? Spring is a time when people are more active, so a few extra calories will disappear in no time. Enjoy life, and keep it sweet! For complete details about Portsmouth Sweet: The Dessert Trail, visit the Visit Portsmouth website.
Hoffler Creek Wildlife Preserve is a 142-acre oasis at the mouth of the James River and connecting to the Chesapeake Bay through Hampton Roads. The preserve is bordered by Hoffler Creek, named after Revolutionary War militia Captain William Hoffler, and the entire area is steeped in rich history. Hoffler Creek Wildlife Preserve functions to conserve the last parcel of wilderness in the Hoffler Creek Watershed consistent with good stewardship for environmental education, research, and recreation. Paddling through the wetlands and watershed is probably the best way to experience this beautiful haven in the middle of urban Hampton Roads. Guided and self-guided kayaking outings are offered at Hoffler Creek. Guests may rent kayaks or bring their own. Space is limited so be sure to register early for any planned kayaking events. This spring, Beginner Kayaking Lessons are offered on April 25 and May 3. The Full Moon Paddle is May 7, Guided Sunset Paddle is May 17, and a guided Early Bird Paddle is May 30. Kayaks may be rented for self guided paddles during regular operating hours. The Preserve offers a variety of other land-based programs as well.
At the south end of Portsmouth, Paradise Creek Nature Preserve also offers kayaking opportunities. A handicap accessible kayak launch is open at the park for non-motorized vessels! The public may bring their own kayak or canoe and explore the 11 acres of restored wetlands, opening into Paradise Creek. Vessels need to be carried a short distance from the far end of the parking lot. Paradise Creek has a number of clear-bottomed kayaks used for their guided kayak outings throughout the year. Paradise Creek Nature Park is a 40-acre waterfront park teaching generations what it takes to bring back the health of an urban river, once presumed dead. It features two miles of trails that lead visitors through an urban forest under revitalization. 11 of those acres represent the largest restored wetland in the area that’s open for public paddles.
Welcome to Atlantic Union Bank Pavilion. Re-opening after two years of renovations later this spring, this 6,500-capacity outdoor venue hosts live entertainment from all musical genres. It’s situated on the Elizabeth River overlooking Olde Towne Portsmouth and the beautiful Norfolk skyline. The venue offers covered and lawn seating, a VIP area, and convenient garage parking. Many guests arrive early and walk up High Street to their favorite restaurant or pub to enjoy dinner and drinks before the show. High Street is a short walk from the Pavilion’s main entrance. Past performances include include Phish, Janet Jackson, Lionel Richie, twenty one pilots, Chris Stapleton, Tom Petty, Anita Baker, Robert Plant, Tony Bennett, Dierks Bentley, BB King and more. This year, the performance schedule is being developed for a vibrant summer season but will definitely include Kevin Gates on June 10 and Buddy Guy with Johnny Lang on July 30.
The Virginia Arts Festival returns to Portsmouth this year with two planned performances so far. On April 28th, the darling of the New York cabaret scene, a protégé of Wynton Marsalis, and the recipient of a host of awards, from the Montreux Jazz Voice Competition to the Thelonius Monk International Jazz Vocal competition, Vuyo Sotashe performs at Roger Brown’s. Tickets are limited for this sell-out event. On May 7th, a morning “Coffee Concert” featuring acclaimed Italian chamber music ensemble Quartetto Adorno will perform in the acoustically delightful sanctuary of historic St. John’s Episcopal Church.
For a different kind of show, see first run films at the Commodore Theater on High Street. This restored 1945 art-deco style theater is on both the national and state historic registers. Downstairs seating is restaurant style and dinner is served at your table during the movie. Upstairs is traditional balcony style theater seating with a concession stand. The restored murals, the crystal chandeliers, and ladies lounge, and the original ticket box make this theater a must see when visiting Portsmouth. Add to that a 42 ft. screen and the only certified Dolby THX sound system in Hampton Roads and it’s the perfect place to see a film. Grab a nightcap on High Street after the show and make it a full evening.
Visit Portsmouth Virginia! The city is located in southeastern Virginia. A part of the Hampton Roads community of cites, Portsmouth is 30 minutes from the Virginia Beach oceanfront, less than an hour from Williamsburg, and we share a waterfront with downtown Norfolk. Don’t miss this Coastal Virginia treasure with its collection of antique homes spanning three centuries, its eclectic assortment of hip shops, edgy nightlife, and saucy, one-of-a-kind restaurants. Olde Towne is walkable, from the Children’s Museum of Virginia to the historic park at Fort Nelson and everywhere in between. Just park the car or show up by boat and head out on foot to explore this funky and friendly little city. Looking for a photo op? Take a walk on the Seawall at night and check out the best city light show in all of Hampton Roads. Portsmouth is a groovy little seaport with a happening art scene and an awesome music pavilion featuring the hottest touring bands. When you’re done with Olde Towne, take a ride to Midtown, Churchland, Truxton, Port Norfolk or any of our other historic communities and see what other offbeat places you can discover. Portsmouth is a laidback old city and a fantastic place to hang out for a day, a weekend, or even a lifetime.