60+ Cape Charles Businesses/Organizations Named Winners of Best of Virginia Campaigns

From fine dining to landscaping, Cape Charles business owners go above and beyond to provide guests and clients with top-notch experiences. This town is made special not by the individual items we procure, but how we use them to create the perfect seaside dish, exquisite spirits, a cozy place to stay minutes from the beach, or a unique display of locally-inspired merchandise. In Cape Charles, everyone is treated like family, precisely why our tiny town of 1,200 boasts 66 winning businesses and organizations across Virginia Living Magazine’s Best of Virginia campaign and Coastal Virginia Magazine’s Best of the Eastern Shore campaign. Oh, and not to mention that the town of Cape Charles won Overall Gold for Best Weekend Getaway in Coastal Virginia Magazine’s Reader’s Choice Awards.

Browse our list of winners & plan your next getaway to Cape Charles!

Best of Virginia Winners via Virginia Living Magazine:

Bailey’s Bait & Tackle : Silver Best Sporting Goods or Outdoor Outfitter

Barrier Islands Center: Gold Best Annual Charity Event (Oyster Roast), Gold Best Museum, Bronze Best Art Event (Art & Music on the Farm)

Bay Creek: Bronze Best Resort, Bronze Best Golf Course

Bay Haven Inn: Bronze Best Bed & Breakfast 

Bayside Chiropractic Rehabilitation & Laser: Bronze Best Chiropractic Practice 

Blue Heron Realty: Gold Best Real Estate Firm

Brown Dog Ice Cream : Silver Best Ice Cream Shop

Cape Charles Beach : Bronze Best Tourist Attraction, Bronze Best Family Entertainment 

Cape Charles Brewing Company: Silver Best Brewery 

Cape Charles Distillery: Gold Best Distillery, Silver Best Cocktails

Chatham Vineyards: Bronze Best Winery 

Chuckletown Productions: Silver Best Children’s Store

Deadrise Italian Kitchen: Gold Best Pizzaria 

Eastern Shore Dog: Silver Best Dog Training Company

Edible Picasso: Silver Best Vegan, Vegetarian, or Gluten Free Fare

Gull Hummock Gourmet Market: Gold Best Specialty/Gourmet Food Shop, Bronze Best Wine Shop 

Historic Palace Theatre: Bronze Best Performing Arts Theatre 

Hook @ Harvey: Silver Best Fine Dining

Jeff Klingel Landscape Design: Silver Best Landscape Design

Kiptopeke State Park: Silver Best State Park 

LemonTree Gallery and Studio: Silver Best Entertainment for Adults

Peach Street Books: Silver Best Bookstore 

The Shanty: Gold Best Seafood Restaurant, Bronze Best Outdoor Dining

Best of the Eastern Shore Winners via Coastal Virginia Magazine:

A1 Seafood: Gold Best Seafood Market 

AJ’s Bar & Grill: Gold Best Casual Eatery, Gold Best Place for Oysters, Gold Best Nightlife, Silver Best Cocktails 

Ambrogia Caffè & Enoteca: Gold Best Dinner (Tie), Gold Best Restaurant Overall, Silver Best Wine Selection 

At Altitude Gallery: Bronze Best Art Gallery, Bronze Best Art Store 

Bailey’s Bait & Tackle: Gold Best Bait and Tackle Store, Gold Best Outdoor Sporting Store 

Barrier Islands Center: Gold Best Historical Attraction, Gold Best Museum, Silver Best Kid-Friendly Attraction

Bay Creek Resort: Gold Best Resort 

Bay Creek Realty: Silver Best Real Estate Agent (Linda Buskey)

Bay Creek Vacation Rentals: Bronze Best Vacation Rental Company (Tie)

Bay Haven Inn: Gold Best Bed and Breakfast 

Beach Market: Bronze Best Seafood Market 

Brown Dog Ice Cream: Gold Best Ice Cream Shop 

Blue Heron Realty Co: Silver Best Real Estate Company 

Buoy 56: Gold Best Women’s Boutique 

Cape Charles Brewing Co: Gold Best Winery/Brewery/Distillery, Silver Best Outdoor Dining, Silver Best Nightlife 

Cape Charles Candy Co: Gold Best Candy Store 

Cape Charles Coffee House: Gold Best Breakfast, Gold Best Coffee, Silver Best Brunch 

Cape Charles Distillery: Gold Best Cocktails, Bronze Best Winery/Brewery/Distillery 

Cape Charles Fishing Adventure: Bronze Best Fishing Guide/Charter (Tie)

Cape Charles Main St: Gold Best Event/Festival (Festive Fridays)

Cape Charles Marina: Gold Best Marina 

Cape Charles Mini Golf: Gold Best Kid-Friendly Attraction  

Cape Charles Museum: Silver Best Historical Attraction, Silver Best Museum

Cape Charles Tiny Livin’: Bronze Best Wedding Venue, Bronze Best Hotel/Motel

Cape Charles Vacation Rentals: Silver Best Vacation Rental Company (Tie)

Chatham Vineyards & Winery: Silver Best Winery/Brewery/Distillery

Chesapeake Bay KOA: Bronze Best Campground  

Chesapeake Properties: Gold Best Real Estate Agent (Kim Starr), Gold Best Real Estate Company, Gold Best Vacation Rental Company (Tie), Bronze Best Real Estate Agent (Eva Noonan)

Chessie’s Toys &  Games: Gold Best Toy Store 

Chuckletown Productions: Gold Best Gift Shop, Bronze Best Toy Store

Citizens for Central Park: Silver Best Event/Festival (Concerts in the Park)

Coastal Baking Co: Bronze Best Bakery 

Coldwell Banker Harbour Realty: Silver Best Real Estate Company (Tie)

Cowlick’s Creamery: Bronze Best Ice Cream Shop 

Cravings Grab-N-Go: Silver Best Lunch

Deadrise Italian Kitchen: Gold Best Pizza, Silver Best Casual Eatery, Bronze Best Dinner 

Drizzles: Silver Best Gourmet/Specialty Foods Store 

Edible Picasso: Gold Best Lunch, Bronze Best Casual Eatery 

Fig Street Inn: Silver Best Bed and Breakfast 

Grant’s Grinds: Bronze Best Coffee 

Gull Hummock: Gold Best Wine Selection, Gold Best Gourmet/Specialty Foods Store 

Historic Palace Theatre: Gold Best Place for Live Entertainment 

Hook @ Harvey: Gold Best Dinner (Tie), Silver Best Restaurant Overall, Silver Best Waterfront Restaurant 

Hotel Cape Charles: Gold Best Hotel/Motel

K-Coast: Gold Best Surf/Skate Shop

Kiptopeke State Park: Gold Best Hiking Spot, Silver Best Place for Birding, Silver Best Campground

Lemon Tree Gallery and Studio: Gold Best Art Gallery, Gold Best Art Store 

Live Local-ISH: Silver Best Vacation Rental Company (Tie)

Local-ISH Art: Silver Best Art Gallery, Silver Best Art Store, Bronze Best Home Goods/Decor

Love Letters: Silver Best Consignment Store, Silver Best Women’s Boutique 

Love Sign: Gold Best Place for Photos; Most Instagrammable 

Mason Avenue Bakery: Gold Best Bakery 

Mimosa Barn: Silver Best Wedding Venue 

Moonrise: Gold Best Jewelry Store 

Poseidon Watersports: Silver Best Water Sport Rental Company 

SHO-NUF Sportfishing: Silver Best Fishing Guide/Charter

Southeast Expeditions: Gold Best Kayak Rental Company, Gold Best Water Sport Rental Company, Silver Best Tour Company 

Sun Outdoors Cape Charles: Gold Best Campground 

Sunset Beach Resort: Bronze Best Resort 

Table & Tonic: Silver Best Gift Shop, Silver Best Home Goods/Decor

Tidewater Charters: Gold Best Fishing Guide/Charter, Gold Best Tour Company 

The Boardwalk: Gold Best Home Goods/Decor, Silver Best Toy Store, Bronze Best Gift Shop 

The Northampton Hotel: Gold Best Brunch, Silver Best Hotel/Motel, Silver Best Breakfast

The Oyster Farm: Gold Best Wedding Venue, Silver Best Place for Oysters, Silver Best Marina, Silver Best Resort, Bronze Best Farmers Market, Bronze Best Seafood Restaurant, Bronze Best Waterfront Restaurant 

The Shanty: Gold Best Outdoor Dining, Gold Best Seafood Restaurant, Gold Best Waterfront Restaurant, Bronze Best Event/Festival (Crab Slam), Bronze Best Cocktails 

Top Dog Charters: Bronze Best Fishing Guide/Charter

Vance’s Furniture Store: Gold Best Furniture Store 

Posted August 7, 2025 by Allie Etheridge

The LOVE Run will be here before you know it! If you’re looking to run your first 5K, get back in shape, or even improve your pace, this training program is for you!

SunMonTuesWedThursFriSat
3/1/26Rest DayRest or CrosstrainRun/Walk
1.0 min ea
X 10		Rest or CrosstrainRun/Walk
1 min ea
X 10		Rest or CrosstrainRun/Walk
1 min each
X 10
3/8/26Rest DayRest or CrosstrainRun/Walk
1.5 min run
2 min walk
X 8		Rest or CrosstrainRun/Walk
1.5 min run
2 min walk
X 8		Rest or CrosstrainRun/Walk
1.5 min run
2 min walk
X 8
3/15/26Rest DayRest or CrosstrainRun/Walk
2 min ea X 5		Rest or CrosstrainRun/Walk
2.5 min ea
X 5		Rest or CrosstrainRun/Walk
2.5 min ea
X 5
3/22/26Rest DayRest or CrosstrainRun/Walk
3 min run
2 min walk
X 4		Rest or CrosstrainRun/Walk
3 min run
2 min walk
X 4		Rest or CrosstrainRun/Walk
4 min run
2.5 min walk
X 3
3/29/26Rest DayRest or CrosstrainRun/Walk
5 min run
3 min walk
X3		Rest or CrosstrainRun/Walk
8 min run
5 min walk
8 min run		Rest or Crosstrain20 min continuous running
4/5/26Rest DayRest or CrosstrainRun/Walk
6 min run
2 min walk
X 2		Rest or CrosstrainRun/Walk
10 min run
3 min walk
10 min run		Rest or Crosstrain25 min continuous running
4/12/26Rest DayRest or Crosstrain25 min continuous runningRest or Crosstrain25 min continuous runningRest or Crosstrain25 min continuous running
4/19/26Rest DayRest or Crosstrain30 min continuous runningRest or Crosstrain30 min continuous runningRest or CrosstrainRACE DAY!

Helpful Tips:

Start each session with a warm up of dynamic pre-run drills or walking to avoid injuries like tearing cold muscles (think cold silly putty verses warm). You’ll know your body is warmed up when your heart rate increases and you break a light sweat.

Remember, soreness after starting a new fitness program is normal. Stretch after your run, cross train between runs and observe your rest days to alleviate the soreness and avoid potential injuries.

Proper nutritian and hydration is paramount to healthy running. Increase your water (not sports drinks) intake when running, if you’re thursty then you’re already dehydrated. Runners should get 60% to 70% of their calories from carbohydrates, with lean protein and healthy fats each accounting for 15% to 20% of their remaining calories.

Listen to your body, some days you will need to walk more than others. If this happens, it may be due to nutritional needs or sleep issues. Compare what you’ve eaten or sleep habits on easy vs difficult days to help narrow down the issue. Also, don’t forget about your hydration, if you’re thirsty then you’re already dehydrated. Be proactive with your water intake.

Control your pace. A good measure is the talk test: you should be able to hold a light conversation (a full sentence). Your pace is specific to you and will be different for everyone. If training with a group, it’s best to default to the slowest member in the beginning.

Cross training with weights helps to improve your speed and endurance while cross training with yoga helps to improve your flexibility and decrease potential injuries. Alternating both on your cross training days are a great way to improve your training experience.

Proper running form will help reserve your energy when running: Head over shoulders/hips, hands down by your hips and open, lift your feet so you’re not shuffling and use your core to maintain your posture.

Don’t focus on distance, instead focus on building your endurance from a run/walk to 30 min of running over the 8 weeks.

Have training questions? Post below for advice from a local sports specialist.

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Training for a race can be mentally and physically exhausting—not to mention all the tech that seems required just to go for a simple run. Smartwatches, heart-rate monitors…the list goes on. With this beginner-friendly guide, you can train simply and confidently to cross the finish line at Cape Charles’ annual LOVE Run on April 25, 2026. Clean, straightforward running to get you race-day ready.

This plan is designed for beginners, walkers-turned-runners, and anyone returning to running after time off.

9-Week Couch-to-5K Transformation Plan:

Weeks 1-2: Alternate 1 minute runs with 2 minute walking periods for 20-25 minutes total, 3 days per week.

Weeks 3-4: Alternate 2-3 minute runs with 2 minute walking periods for 25-30 minutes total, 3 days per week.

Weeks 5-6: Run for 5-8 minutes with short walk breaks for 30 minutes total, 3 days per week.

Weeks 7-8: Run for 20-30 minutes consistently, practicing race-day pace, 3 days per week.

Race Week: Two easy, short runs. Rest the day before the race.

Tips & Tricks:

  • Your running pace should feel conversational—you should be able to talk, even if it’s in short sentences. If you need to slow down, slow down. That’s part of the plan.
  • Rest days matter just as much as run days. Take extra rest if your body needs it, and don’t be afraid to repeat a week before moving on.
  • Remember, this schedule isn’t about perfection—it’s about consistency. You don’t have to be fast; you just have to start.

Start where you are. Train simply. Run with love on April 25.

Unwind and relax this winter in Cape Charles, Virginia. With the summer rush long gone, this quiet season invites you to slow down and experience the Shore at its most peaceful. Cozy bed & breakfasts have vacancies, the sidewalks are calm, and downtown feels warm and welcoming. Local boutiques offer one-of-a-kind shopping opportunities, perfect for finding handmade gifts or treating yourself to something special.

A stroll along the empty beach provides space to breathe and space for your dogs to run free. Winter tides bring freshly washed-up shells, making this the best season for beachcombing. Back in town, boutique owners and artisans are eager to share their stories: how their goods are made, what brought them to Cape Charles, and the history that shapes their work. This is the time of year when visitors move beyond sightseeing and truly connect with the people, culture, and pace of life in Cape Charles.

This season also brings its own lineup of unique events. Celebrate New Year’s Eve at the Cape Charles Crab Pot Drop or take the plunge at Freezin’ for a Reason. Out on the trails, Kiptopeke State Park and the Eastern Shore National Wildlife Refuge offer peaceful walks with the chance to spot winter waterfowl, migrating birds, and quiet coastal landscapes at their most serene.

While many restaurants adjust their hours in the off-season, there’s still a warm, welcoming place to enjoy every meal. From breakfast and coffee shops to dinner spots serving local seafood and winter comfort dishes, the slower pace gives you more time to savor each experience.

Fresh air, fresh food, and fresh finds make for a peaceful and refreshing start to the new year on Virginia’s Cape. Whether you’re seeking a quiet weekend escape or a meaningful reset after the holidays, Cape Charles offers a winter retreat unlike anywhere else on the Eastern Shore.

Allie Etheridge

December 8, 2025.

The most magical time of the year is right around the corner, and Cape Charles Main Street invites you to celebrate the season with Festive Fridays — our cherished Holiday Tradition filled with free, family fun for everyone! Join us every Friday from November 28 through December 19 as our charming downtown transforms into a winter wonderland bursting with holiday cheer.

Each Friday evening, the streets of Cape Charles come alive with twinkling lights, joyful laughter, and the spirit of the season. From parades and holiday music to Santa and Mrs. Claus greeting families with warm smiles, there’s no better way to make lasting memories with loved ones.

Enjoy a lineup of free activities designed to delight visitors of all ages. Climb aboard our festive train rides for a magical journey through town, stop by the petting zoo for some animal fun, or let your little ones get creative with children’s crafts. You’ll also find talented street performers, a whimsical balloon artist, and a skilled caricature artist ready to capture your holiday spirit in a one-of-a-kind keepsake.

Don’t forget to cozy up for free showings of classic holiday movies—the perfect way to relive the magic of your favorite seasonal stories. And of course, a trip downtown wouldn’t be complete without a little holiday shopping! Stroll through Cape Charles’ boutiques and specialty shops, where you’ll find unique gifts, festive décor, and plenty of local charm to fill your stockings.

Whether you’re sipping hot cocoa while watching the parade roll by, taking selfies with Santa, or discovering the perfect handmade present, Festive Fridays promise something special for everyone. Best of all, every activity is free, thanks to the support of Cape Charles Main Street and our incredible community partners and volunteers!

So gather your family, bundle up, and make Cape Charles your destination for festive fun this holiday season. Come experience the magic, laughter, and togetherness that make Festive Fridays a tradition worth celebrating year after year.

Mark your calendars: Fridays, November 28 – December 19, right in the heart of downtown Cape Charles. For information on other amazing events like our Historic Holiday Cookie Trail on December 13, please check out our event calendar HERE.

Free. Festive. Family Fun. That’s what the holidays are all about!

Laughing King Oyster Company owner and founder, Thomas, harvests oysters.

Welcome to Virginia, the East Coast’s oyster capital—so abundant that swimmers once feared the inevitable scrapes from their sharp shells. Today, Virginia remains home to a rich variety of oysters, with the Eastern Shore boasting four distinctive types: the Seaside, the Upper and Lower Chesapeake Bay Eastern Shore, and the Tangier. Each carries its own flavor, shaped by the waters where it grows.

The Eastern Shore takes pride in its iconic fishing heritage, built on the bounty of the water. Few traditions capture that spirit better than the oyster roast. Whether you’re gathered around a grill with family and friends or enjoying oysters to the sound of live music, these roasts are a true celebration of community and season. Below, you’ll find some of the Shore’s classic fall oyster roasts.

Saturday, October 11, 2025
Chincoteague’s 52nd Annual Oyster Festival is the ultimate fall escape. Presented by the Chincoteague Chamber of Commerce, the festival shines a spotlight on the seafood industry and marks the official start of oyster season. Tickets are $65 per person and include all-you-can-eat oysters on the half shell, steamed, fried, and frittered, plus a hearty non-oyster menu. While you dine, enjoy music by Island Boy, a festival favorite for over 30 years, and don’t miss the Extravaganza Raffle, offering a grand prize valued at thousands in merchandise and certificates.

Saturday, October 18, 2025
The Town of Saxis invites you to its annual oyster roast, a beloved fall tradition. Feast on all-you-can-eat steamed and raw oysters, with BBQ on hand for the non-seafood crowd. The Shoreline Groovers will keep the music lively, and the Saxis Island Museum will share the island’s history at their booth. A raffle with exciting prizes rounds out the day. Proceeds benefit community beautification and improvement projects across Saxis Island.

Saturday, November 1, 2025
The Cape Charles Museum welcomes guests to its Annual Oyster Roast fundraiser. Whether raw, roasted, or served with a twist, the oysters here highlight the Shore’s freshest catch. Guests will also enjoy fine wine, additional bites, local music, a silent auction featuring one-of-a-kind items, and a lively 50/50 raffle. All proceeds support the Cape Charles Historical Society.

November 1, 2025
The Island House of Wachapreague hosts its annual oyster roast benefiting the Navy SEAL Foundation. Known for big flavors and even bigger entertainment, the event has welcomed top-tier talent in past years, including The Brothers Osborne in 2021.

Can’t make the festivals? Make your own roast.
It’s easier than you think to bring the Shore’s signature tradition home. Purchase a bag of oysters from local favorites like Cherrystone Aqua-Farms, Beach Market, or A1 Seafood. Steam them on your stovetop or roast them over an outdoor grill, then gather friends around a bonfire for a true Eastern Shore experience.

Curious before you commit? Take an oyster tour.
If you’re not quite ready to dive into the briny bite, eco-tour operators offer hands-on oyster experiences during the warmer months. Laughing King Oyster Company at Vessel Farm, for example, provides an educational tour aboard their oyster barge. Learn how aquaculture works, see the growing process up close, and even taste an oyster pulled straight from the water.

This fall, celebrate Virginia’s oyster culture on the Eastern Shore. Whether at a festival, around your own grill, or out on the water, there’s no better way to savor the season.

Laughing King Oyster Company Oyster Portrait.

Oysters on ice at The Shanty.

Oysters on ice at The Shanty.

Posted on October 7, 2025 by Allie Etheridge.

Cape Charles is more than just a summer hideaway. When the temperatures cool off, Cape Charles is still here, businesses bustling, golf carts rolling, and adventures awaiting. We’re here to tell you all of the reasons you should visit Cape Charles in the off-season.

Avoid the crowds: Hate waiting in lines? Traveling to Cape Charles in the off-season ensures you will have first-class access to the town. Don’t worry about calling ahead for dinner reservations, how long the check out line is at your favorite store, or getting to the bakery early. Just show up and revel in the greatness of a blissfully uncrowded Cape Charles.

The beach never closes: The water may not be a comfortable temperature for swimming, but our beautiful beach still offers an escape. Stroll around looking for shells, go on a beach run, or watch one of our spectacular sunsets to soak in our sandy coastline. The beach isn’t just for swimming, make it yours!

Year-long events season: You might know us for our Saturday night concerts in the park, annual Crab Slam, or July 4th celebration, but did you know we have unforgettable events all year long? In October, Dock Dogs brings tail-wagging, high-flying fun to town as our furry friends compete to win a tournament. At the end of October, our spooky secrets come alive as Cape Charles is haunted at the Halloween Hootenanny. November brings holiday spirit when Festive Fridays begin, four consecutive Friday nights of holiday fun on Mason Avenue. February highlights Love the Locals Week, a week of specials, promotions, and discounts at local businesses. And in April, join us for our annual LOVE Run, featuring a 10K, 5K, and 1-mile color run. Not to mention all of the fantastic events our businesses put on!

Observe unique wildlife: The early fall is the best time to see wildlife on the Eastern Shore of Virginia. Witness the fall migration of hawks, falcons, herons, egrets, and more from one of our nearby nature preserves. And as winter settles in, stick around to see cold-weather waterfowl like snow geese, tundra swans, or bufflehead ducks.

The opportunities are endless: No matter where your interests lie, Cape Charles has something for everyone! Outdoorsy? Try kayaking through our marshland, touring Fisherman’s Island, or hopping on a fishing charter. Girls trip? Head over to Chatham Vineyards and Winery or shop the local boutiques in our Historic Shopping District. Need fun for the whole family? Grab dinner at Cape Charles Brewing Company, see a show at the Historic Palace Theatre, or simply cruise around town on a golf cart.

Fall in Cape Charles just has a certain type of charm to it. From scenic backroads to breezy mornings on the porch, the off-season in Cape Charles offers unrestrained access to all the Eastern Shore has to offer. Stay a while in Cape Charles and discover what makes our town special year-round.

From the tranquil creeks of the Eastern Shore to the Chesapeake Bay and Atlantic Ocean, there are many ways to enjoy the beautiful waters surrounding Cape Charles. Whether you’re craving a peaceful paddle or a fun fishing adventure, here are some of our tried-and-true suggestions for excursions that are worth leaving the Shore for — any time of year.

The Schooner Windsong

Schooner Windsong is a family-owned and -operated sailing business that specializes in two-hour private sunset charters and public day sails for up to six people. The cruises depart from Cape Charles Town Harbor and sail out along the town beach and into the Chesapeake Bay. In addition to two-hour charters, they also offer whole- and half-day sailing trips with the option for a catered boxed lunch, and they’re adding private and small-group sailing lessons this year. “Our captains and crew have extensive knowledge of the history and wildlife of Cape Charles and the Chesapeake Bay, so feel free to ask any questions or even jump in to handle lines or grab the tiller and steer the boat,” says owner Bronwyn Comer. “Our favorite thing about sailing the waters from Cape Charles has to be the sunsets. The Eastern Shore of Virginia is unique in that it’s one of the few places on the east coast of the U.S. where you can experience the sunset over a large body of water.” You can also expect to spot local wildlife such as dolphins and sea turtles. Bronwyn recommends booking as soon as you have a date in mind, especially for the sunset trips, which sell out quickly. Find out more at schoonerwindsong.com.

Tidewater Charters

Tidewater Charters is a year-round guide service on the Eastern Shore of Virginia specializing in light tackle fishing and tours. “We fish for everything that swims in the Bay, but we focus our efforts on speckled trout, striped bass, red drum, and cobia,” says Captain Tyler Nonn. “Our tours on the Bay and seaside have become very popular as well. Exploring one of the last undeveloped coastal areas on the entire East Coast is a very unique experience.” Tidewater Charters has five charter boats including one boat solely dedicated to cruises and four fishing boats. They can accommodate groups of up to 15 or potentially more. Tyler says his favorite times of the year to go out on the water are fall and spring. “There’s just a lot of fishing options and diversity in species to catch which makes it a lot of fun.” He recommends booking a season ahead, especially for holidays and weekends. Find out more at twcharters.com. 

Southeast Expeditions

The adventure experts at Southeast Expeditions have been sharing the wonders of the Shore with visitors for more than 20 years. They offer rentals of kayaks and paddleboards, with delivery included, as well as guided tours of the waters around Cape Charles. A firm favorite is their Paddle Your Glass Off Tour, a guided kayaking tour that takes paddlers through Church Creek to Chatham Vineyards. Participants are rewarded with wine and a cheese tray before paddling back. Find out more at southeastexpeditions.com. 

Cape Charles Community Sailing

Dedicated to teaching the art of sailing to people of all ages, Cape Charles Community Sailing offers junior summer sailing camp as well as private sailing lessons that cater to families, kids, and adults. Meeting at the Oyster Farm Marina, CCCS is run by Hannah Twiddy, a longtime sailor who grew up in Elizabeth City, N.C. Their newest offering is an Eco Sailing Camp intended to educate participants about local watersheds in the Chesapeake Bay and beyond. Find out more at capecharlessailingcamp.com.

If your visit to Cape Charles feels incomplete without taking in some live music, you’re in luck — the town regularly hosts talented musicians in venues all over town. Whether you’re in the mood for an intimate gallery show or a big blowout concert in the park, there’s entertainment for every type of music fan. Keep an eye on our Events Calendar to see what’s coming up — and here are just a few shows that deserve a spot on your schedule!

Friday Nights at Lemon Tree Gallery

Fridays from 6:30-8:30 p.m. 

Lemon Tree Gallery, 301 Mason Ave.

Free

Lemon Tree Gallery is the place to be on Friday nights, when art fans and music lovers are treated to a few fun hours of free live entertainment. From 6:30-8:30 p.m., stop in to enjoy tunes from regional acts like guitarist Art Rowe (April 12), the Shoal Shakers (May 10), and the Stingrays (May 31). See the full schedule here. 

ESVA ChamberFest

May 18, 3-8 p.m.

Cape Charles waterfront

$78

Don’t expect any chamber music at this highly anticipated outdoor music fest, hosted by the Eastern Shore’s Chamber of Commerce. The 21+ “premier tailgating event” features performances from the Little River Band, Firefall, and the Irie Tree Band. Find more info here.

 Wilder Horses: A Rolling Stones Tribute

June 1, 7:30 p.m.

Historic Palace Theatre, 305 Mason Ave.

$30, $15/students

The Palace Theatre once again welcomes Rolling Stones tribute band Wilder Horses for an unforgettable performance of the band’s most classic hits. From the Mick Jagger clone lead singer to period instruments and costumes, the band offers fans an immersive blast from the rock ‘n’ roll past. This is another production of Arts Enter Cape Charles. 

Concerts in the Park

Saturdays from June 22 through Sept. 7

7 p.m.

Central Park

Free

Hosted by Cape Charles Citizens for Central Park, this beloved annual summertime event brings a wide variety of musical acts to Cape Charles for free, family-friendly shows in scenic Central Park. This years line-up includes acts like Forest Hill, the Deloreans, and Brasswind — you can see the full schedule here. Bring a lawn chair and your dancing shoes. Food and drinks are available to purchase at the event.

Sail on, The Beach Boys Tribute

Saturday, August 3, 7:30 p.m.

Historic Palace Theatre, 305 Mason Ave.

For tickets, visit www.artsentercapecharles.org or click on this link Buy Tickets Here

$30, Students $15

Cape Charles will be transported to 1960s-era with The Beach Boys tribute band Sail On. They will be performing all of the classic hits, plus some treasures from the brilliant extended catalog, Sail On faithfully recreates the soundtrack to an Endless Summer live and in rich detail.

Arts Enter Cape Charles

LoveFest

August 31, 7 p.m.

Central Park

Free

Lovefest returns to Cape Charles on Labor Day weekend with a performance from The English Channel, a British invasion band known for playing pop, rock, and prog hits from the 1960s and 1970s. This annual event in Central Park encourages concert-goers to dress in their best ‘60s swag to enjoy the music along with food trucks and wine, beer, and a specialty Love Potion cocktail. 

With its gentle terrain and spectacular scenery, Cape Charles is a paradise for runners any time of the year. But there’s one day that stands out in our calendar: LOVERun day! Scheduled for the morning of April 20, the 2024 LOVERun is a family-friendly run that takes participants through the streets of historic Cape Charles and along the waterfront. For the first time this year, runners can choose between a 1 mile color run and 5K or 10K timed options. Proceeds from the LOVERun help to fund Cape Charles Main Street initiatives that benefit the town.

Participants in the 1 mile color run will be periodically sprayed with vibrant colors – and don’t worry, they’re completely safe and environmentally friendly. The 5K and 10K races will have staggered starts; neither of these races is a color run. After the races, participants and their cheering squads can gather at the Cape Charles LoveWorks sign for a party featuring live music, food trucks, beverages and family fun. 

So how can you prepare for the LOVERun in Cape Charles? Here are six tips:

  • Set realistic training goals for yourself. Remember – this is a fun run. And you can even walk the entire route if you want to! But if you’re planning to run the entire race, you may need to do some training to prepare. Both seasoned and amateur runners can benefit from planning and preparation, although your approach should vary based on your fitness level. Try to run a few times a week in the month or two leading up to the race, gradually increasing your distance and intensity as race day nears.
  • Practice running the route. The run will take participants throughout the historic district of Cape Charles, down Mason Avenue, around Central Park, and along the bayfront. If you’re local, you’ll have the benefit of being able to practice running the route leading up to the race and identifying any challenging areas. If you’ll be visiting for the race, try practicing on similar terrain in your own neighborhood or even on a treadmill. When you arrive in town for the race, it may give you some peace of mind to check out the race course by car, bike, or even golf cart the day before.
  • Fuel your body. Forget carbo-loading before the race. The best thing you can do for your body is to eat what you normally eat before you run — ideally something that won’t upset your tummy. And hydrate! 
  • Dress the part. Participants will receive pre-ordered T-shirts with their race packets, but make sure you are prepared with comfortable, broken-in attire — this isn’t the time to try out a new pair of shoes! Be sure to check the forecast before the race as weather on the Eastern Shore can be unpredictable, especially in the springtime. You can expect anything from rain and blustery winds to heat and harsh sunshine.  
  • Warm up and cool down. Give yourself at least five minutes before the race to warm up with dynamic stretches and cool down afterward with stretching or a brisk walk.
  • Make sure you’re registered! The LOVERun is fun and casual, but you do have to register to participate! Be sure to register here in the proper category (10K, 5K, or 1 mile and choose adult, youth, child) before the registration deadline.
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