Planning the Ultimate Guys’ Weekend in Cape Charles

Whether you’re planning a fishing trip, a laid-back bachelor party, or you’re just in dire need of some “bro time,” Cape Charles is tailor-made for a mancation to remember. This beach town on Virginia’s Eastern Shore offers a wealth of outdoor activities, great dining, and an award-winning brewery, so gather your friends and pack your bags for the ultimate guys’ weekend in Cape Charles.

When to Plan Your Guys’ Getaway

Cape Charles is a great destination any time of year, so you’ll want to schedule your guys’ trip based on what you want to do with your time. If watersports and lounging on the beach are your idea of a good time, be sure to book your accommodations early for the popular summer months. If you’re into fishing and more of a relaxed vibe with fewer crowds, plan to visit in the off-season — this saltwater fishing guide will tell you what’s in season when.

Where to Stay

Your accommodations of choice will largely depend on the size of your group. A local hotel, B&B, or inn may be ideal for smaller groups, while larger crews may prefer to book a vacation rental home. You can find more guidance on where to stay in Cape Charles right here. There are also lots of places that are listed for rent through VRBO or AirBnB like this home situated just .3 miles outside of Cape Charles Historic district Fish Tales. If you’re willing to stay a bit futher out of town, there are great motel options including Cape MotelPeacock Motor InnShore Stay Suites, Edgewood Motel, Cape Charles Milestone Lodge and for a unique experience Cape Charles Tiny Livin’

What to Do

You guessed it: Fishing is a huge draw for many visitors to Cape Charles. Head to Bailey’s Bait & Tackle shop for the lowdown on what’s biting and to pick up the supplies you need. You can keep it simple by heading to the free town fishing pier, or if you’d like to target some big fish, consider booking a fishing charter either out to sea or in the Bay. Tidewater Charters and Top Dog Charters are just a couple of options that depart from Cape Charles Harbor. Is fishing not your forte? Depending on the time of year, you can plan to fill your days lounging on the beach, hiking or biking local trails, or touring the local watering holes. Speaking of which…

Where to Drink

Cape Charles isn’t a party town, but if cozy pubs and high-quality craft beer and cocktails are more your style, you’ll feel right at home here. With a diverse lineup of brews, a crowd-pleasing menu, and a sprawling outdoor space, Cape Charles Brewing Company is a favorite stop for beer lovers. Cider fans will have fun exploring the creative options at Buskey Cider by the BayKelly’s Gingernut Pub and AJ’s Bar & Grill are popular picks for pints with a side of darts and wings. For something stronger, Cape Charles Distillery has an excellent whiskey selection — enjoy a craft cocktail by their fire pit or pick up a bottle to drink at home.  

Where to Eat

No guys’ trip would be complete without a few memorable meals, and luckily there are plenty of restaurants to choose from in Cape Charles. For a night in, order a stack of pizzas from Deadrise Pies, or head out for a casual seafood dinner overlooking the water at the Shanty or the Oyster Farm. Find pub fare at Kelly’s, AJs, or Cape Charles Brewing Company. Find more info on where to eat in Cape Charles here

Dining on fresh seafood is a quintessential Cape Charles experience. With the Chesapeake Bay to our west and the Atlantic Ocean to the east, we’re surrounded by one of the richest oyster and seafood regions in the country. Whether you want to enjoy seafood at a local restaurant or prepare it yourself at home, you’ll find plenty of options for satisfying your seafood cravings in Cape Charles.

Eastern Shore Seafood Specialties

Though you may find imported seafood on some menus, opt for local specialties if you want the freshest, most delectable dining experience. Luckily, there’s no shortage of these, no matter the time of year. Here are a few must-try Eastern Shore seafood favorites:

  • Oysters
  • Clams
  • Rockfish
  • Blue Crabs
  • Flounder
  • Croaker
  • Sugar Toads/Swelling Toads

Local watermen recommend keeping your eye out for seasonal seafood specialties. From May through September, soft shell crabs are in season. March through November is best for hard crabs. And that rule about only eating oysters during months that end in the letter R? It’s true wild oysters are best October through March.

Seafood Restaurants in Cape Charles

If you’d rather let someone else prepare your seafood, you’ll find several options in Cape Charles. The Oyster Farm and Seafood Eatery is a waterfront restaurant with a raw bar specializing in fresh local oysters. Seafood fans also love their ESVA Clam Chowder, Seafood Fra Diavolo, and Wood-Plank Scallops with risotto. Situated right on the Marina, The Shanty is another popular seafood destination for lunch or dinner. We love their Fried Oyster Po’ Boy and spicy Angry Clams. Cape Charles Brewing Company has a great Rockfish Sandwich and a Cobb Island Crab Cake Sandwich. Head to Kelly’s Gingernut Pub for She Crab Soup packed with local blue crab or the decadent Crab and Brie Pub Burger. For a more upscale waterfront experience, Hook at Harvey has a regularly rotating menu that always features a fresh fish du jour. Salt and Sand Family Restaurant on Peach St. is proud to offer local fish on their daily lunch and dinner menus. Enjoy soft shell crab bites and other local seafood dishes at A&J’s Bar & Grill on Peach St. in Cape Charles as well. 

Shop for Eastern Shore Seafood to Prepare at Home

Preparing your own seafood feast at home is a memorable part of any visit to the Eastern Shore. If you’re seeking fresh seafood in Cape Charles, these are a few of our favorite options:

  • A1 Seafood – Also located on Lankford Highway, carries a wide variety of fresh local seafood and shellfish options – including steamed crabs and shrimp!
  • Beach Market – You’ll find this source of local seafood right on Stone Rd. in Cape Charles. Check the website for what’s fresh as well as deliciously prepared foods
  • Cherrystone Aquafarms — Shop for fresh oysters and clams at this fifth-generation aquafarm located just outside of Cape Charles. They offer delivery and local pickup.
  • HM Terry — With its headquarters in nearby Willis Wharf, this family-owned company specializes in Sewansecott-brand clams and oysters — and has done since 1903.
  • Nottingham Clams and Seafood — Located on Lankford Highway, this seasonal market specializes in local clams, crabs, fish, and more.

Anyone else we’d like to list that’s open to the public?

When Jo Bawiec moved to Cape Charles with her partner, Lori Smith, in 2019, it seemed that hardly anyone in town had heard of pickleball. The pair had fallen hard for the sport while living in Richmond, and they were determined to bring pickleball to their new hometown. Three years later, Jo and Lori have embraced the role of Cape Charles’ pickleball ambassadors, teaching clinics, hosting leagues, and running a Facebook group with more than 300 members.

If you’ve managed to miss the nationwide buzz surrounding pickleball, it’s an addictive sport that combines elements of tennis, badminton, and ping-pong. It’s played with a paddle and a plastic ball with holes, and can be played as doubles or singles. “What I love about pickleball is the social and competitive aspects of the sport,” Jo says. “It’s fun, it’s fast, and a great way to meet other people. You don’t have to be a strong athlete to play. Someone could learn to play pickleball in about 30 minutes and have fun… We have grandparents playing with their grandchildren — How great is that?”

Early on, Jo, Lori, and Debi Facciolli, another Cape Charles pickleball player, started offering pickleball lessons in the hopes of increasing local interest. “At the time, a town official shrugged off the idea of pickleball, saying that we’d probably have the same three people,” Jo laughs. “Well, fortunately, that was very wrong.

“I think our first group had about 12 people in it,” she adds. “Through the last few years, we’ve had many more classes in town and at Bay Creek. I would estimate about 100 folks have been instructed how to play pickleball between the three of us.”

The Cape Charles pickleball Facebook group has been a powerful way to connect pickleball lovers across the Eastern Shore. “We have dedicated pickleball times on the town courts and dedicated tennis times,” Jo says. “These dedicated times allow each group to share the courts respectfully and schedule times to play without interference. This allows both groups to grow and play.” Pickleball has open play time Monday through Friday from 4-7 p.m. and Saturday and Sunday from 12-4 p.m. “This means that anyone who plays can come out to the courts and rotate into games,” Jo says. “This is more recreational play and is a great way to get moving and have fun and be social.”    

The Pickleball League is a way to group players together who are of similar skill levels. There are three groups of eight players each, including advanced beginner, intermediate, and advanced. The leagues play in a round-robin format.

While the group has made great strides in bringing local pickleball fans together, it’s also been beneficial for visiting pickleball fans. “Our local group is a very welcoming group, and we like to see new players come out to give it a try,” Jo says. “Through our Facebook page, we have many tourists reach out to find out where and when they can play. We just recently had a group of 20 players cruise here from Annapolis that wanted to play with the local group. Pickleball players often seek out tourist destinations that offer pickleball. It’s wonderful that Cape Charles is on the pickleball radar now.” 

In Cape Charles, you can now find courts both at Central Park and at Bay Creek. Keep an eye on the Pickleball by the Bay Facebook page for information on meetups as well as free informal clinics that take place a few times a year. “There is a super high demand right now,” Jo says. “If anyone is interested in playing or learning more about pickleball, please reach out or come on out to the courts. Be careful though, pickleball is addicting.” 

Cape Charles Main Street is pleased to announce our annual Love Run will be held on Saturday, April 22, 2023! Our family-friendly 5K COLOR run/walk and first-ever inaugural timed 10K race will take participants through the historic downtown of Cape Charles overlooking the Chesapeake Bay. Runners and walkers can pass through color stations, IF THEY CHOOSE, and be sprayed with bright, fun, harmless, and environmentally safe colors! Our 5K and 10K runners will be timed and there will be prizes for overall and age category winners!

This annual fundraiser will benefit the beautification of our town, including the maintenance of the Love Sign, promote economic vitality for local merchants, and sponsor young local runners to participate.

After the race, join us by the love sign for live music, celebration, fun family activities, and an awards ceremony.  Of course, we’ll also have food, water, beer, mimosas, and bloody marys! 

DATE: Saturday, April 22, 2023, 

TIME: 10K begins at 9:00, 5K begins at 9:30

LOCATION: Corner of Bay and Mason Avenue at the Cape Charles Beach Front by the Love Sign!

REGRISTRATION & PACKET PICK-UP: Registration will be held at the front porch at Northampton Hotel on Friday, April 21st from 4:00 pm to 6:00 pm. Those who can not do advanced pick-up can get their packets on the day of the race at registration. Please bring your QR Code for check-in.


7:30 a.m. Registration and Packet Pick-up Opens @ The Love Sign

8:45 a.m. Registration and Packet Pick-up Closes

9:00 a.m. 10K Race Begins

9:30 a.m. 5K Family Fun Color Run & Walk Begins 

10:00 a.m. Live Music Begins

11:00 a.m. Kids Dash Race

11:30 a.m. Awards Ceremony

1:00 p.m. Post Race Party ends


Early bird $50 10K and $35 5K until March 14th / $65 10K and $40 5K until April 20th / $25 5K Youth (ages 9-15 years old)

Register today!


Performance T-shirts are included for all registered 5k and 10k participants! Excluding youth participants 8 years or younger who are accompanied by an adult and can register for free. 


Advance packet pick-up will be at the Northampton Hotel on Friday, April 21st from 4:00 pm to 6:00 pm. Those who can not do advanced pick-up can get their packets on the day of the race at registration.


Information coming soon! Check back.


Participants can park on Mason Avenue, Bay Avenue, or any one of our close residential streets. No parking pass is required! 


Like this page and invite your friends on Facebook.


We are looking for volunteers and cheerleaders to help guide participants on the course and manage the water and color stations. If you would like to volunteer, please contact our volunteer coordinator Susan Burger


We are always looking for corporate sponsors and donations to make this event a success for more than 300 race participants! Color stations, water areas, start/finish lines and the post-race party will provide ample exposure for donors to create a large presence at this Eastern Shore Spring kick-off event. If you are interested in sponsoring please contact Tara Ashworth. 


If you have any additional questions or concerns please Contact us. 

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Whether you’re arriving to Cape Charles via boat or bringing your boat along on your Eastern Shore vacation, you’ll find that the town is very boater-friendly. Here’s what you need to know about bringing your boat to Cape Charles.

Where to dock your boat in Cape Charles

There are a few options for docking your boat in Cape Charles. Cape Charles Yacht Center is known as the premier Chesapeake Bay marina and boatyard. Its 18-foot-deep channel can accommodate vessels of all sizes, including megayachts. Cape Charles Harbor, managed by the Yacht Center, hosts commercial and recreational vessels with 1200 feet of dock space and 95 slips. Another option is the Oyster Farm Marina, which boasts 124 fully cushioned slips that can accommodate vessels up to 150 feet.

Boat launches near Cape Charles

Just looking to launch your boat in or around Cape Charles? There are plenty of places to begin your exploration of the Chesapeake Bay, whether you’re looking to do some fishing or just taking a pleasure cruise. You can find a list of all of Northampton County’s boat ramps here.

  • The Wise Point Boat Ramp is located within the Eastern Shore National Wildlife Refuge. If offers access to both the Chesapeake Bay and the Atlantic Ocean by way of the Virginia Inside Passage.
  • There is a boat ramp at Kiptopeke State Park offering easy access to the legendary fishing around the park’s concrete ships. 
  • Launching and hauling boats from the ramp at the Cape Charles Harbor is free. The ramp gets busy during warmer months, and boaters should also plan in advance for parking and trailer storage.
  • If you’re heading offshore to explore the Barrier Islands, Oyster Harbor is a great place to start. There’s no fee to launch from here.

Boating safety around the Eastern Shore

The tidal marshes, underwater grass flats, and strong winds that are common in the area can present a challenge to even experienced boaters. Be sure to keep an eye on the weather as well as the tides to avoid getting caught out in the open by a storm, or being stranded by the tides. If you’re exploring the Barrier Islands, the best time to do so is on a rising tide. Also keep an eye out for “No Trespassing” signs to avoid landing on private property, and be aware that some islands may be closed periodically to protect nesting birds. 

Somewhere between the beach bums and the seafood seekers on Virginia’s Eastern Shore, you’ll find another group of visitors drawn to one of the area’s more unique attractions: Birdwatching. Whether you’re an experienced birder or just a beginner, you’ll discover an impressive array of bird species in and around Cape Charles.

Why is the Eastern Shore a destination for birders? To find out, we chatted with Martina Coker of Birding Eastern Shore

Cape Charles Main Street: What is so special about birding on the Eastern Shore? 

Martina Coker: The Eastern Shore provides an exceptional location for birding, with its location on the Atlantic Flyway. Birds heading south on the fall migration funnel through the narrow peninsula, often hesitating prior to heading over the Chesapeake Bay. The resulting staging area allows birders a great opportunity to observe the birds as they wait to cross. There have been 439 bird species recorded on the Eastern Shore. Winter brings large numbers of waterfowl to the area. The spring migration is not as dramatic as the fall, but has a magic of its own, as birds return or pass through on the way to their summer homes. 

CCMS: What are some of your favorite places around Cape Charles to look for birds?

MC: The large amount of conserved land on the Eastern Shore provides varied habitat for birds living in and moving through the peninsula. Visitors to Cape Charles will find many locations to bird, from the Chesapeake Bay Bridge-Tunnel at the southern tip of the peninsula to the Chincoteague National Wildlife Refuge near the Maryland border.

Twenty-six excellent birding locations are listed on the Birding Eastern Shore website. Each location has a description of birds and other wildlife seen at the location, along with details that make it easy to plan your visit. 

There are some great birding areas very close to Cape Charles including Cape Charles Harbor itself. On recent visits, I saw an Eared Grebe (a rare visitor), Greater Scaups, Long-tailed Ducks, Buffleheads, Common Loons, Horned Grebes, American Oystercatchers and a Savannah Sparrow. 

There are usually nesting Ospreys on pilings in the harbor, providing a nice show while you dine at The Shanty. Other great locations nearby include: 

Cape Charles Beach

Cape Charles Natural Area Preserve

Custis Tombs on Plantation Creek

Eastern Shore of Virginia National Wildlife Refuge

Fisherman Island Wildlife Refuge

Indiantown Park

Magothy Bay Natural Area Preserve

Northampton County Nature Preserve

Savage Neck Dunes

Brownsville Preserve

The Village of Oyster

Willis Wharf Overlook

The hawkwatch at Kiptopeke State Park runs from September 1 through November 30 each year. Immense numbers of migrating raptors are counted by on-site biologists over the hawkwatch platform. Visitors are welcome to join the biologists as they document the migration and provide education for visitors. 

The above locations are all in Northampton County, within 30 miles of Cape Charles. The Volgenau Virginia Coast Reserve’s 14 Barriers Islands also provide prime birding locations. There are several captains, who are also certified ecotour guides, who can take you to the islands including Eastern Shore Boat Tours LLC, Seaside Ecotours, and Broadwater Bay Ecotours. Kayaking provides another spectacular way to get close to birds in and around the extensive network of waterways on the shore. Virginia Water Trails provides good information to access kayak trails throughout the Eastern Shore.

Cape Charles and the surrounding area provide visitors with an incomparable birding experience. Birding trips can be enhanced by visits to restaurants such as The Shanty and The Cape Charles Brewing Company, and capped off with delicious ice cream at Brown Dog Ice Cream.

Find out more at Birding Eastern Shore.

Picturesque vista from a trail in Cape Charles

We all love Cape Charles in the summer. From Memorial Day to Labor Day, this little beach town truly shines with summer concerts in the park, sunny days on the sand, spectacular sunsets, and lazy nights cooled by Bay breezes. But when the summer visitors have packed their bags, the town and all of its attractions remain. And that’s when some folks will tell you that Cape Charles shines the brightest: in the off-season.


Why should you visit Cape Charles in the off-season? Whether you’re considering a visit in the winter, spring, or fall, here’s why Cape Charles will never disappoint.


Crowds are thinner. Although Cape Charles rarely feels over-crowded — even in the height of summer — crowds are much thinner in the off-season. Shoot for the shoulder season (late spring and early fall) to enjoy all the benefits of the town’s beautiful public beach without worrying about finding the perfect spot on the sand.


Dining out is easier. No one loves being waitlisted at a restaurant or waiting in line for ice cream, but unfortunately it’s just a fact of life during the peak season in Cape Charles. But in the off-season? You’re a lot more likely to walk right in and claim a table at your chosen restaurant — and to receive quick, friendly service. Just be sure to check seasonal hours — some businesses do close for part of the year.


Two words: Oyster season. You can eat oysters any time of year, and some of the best are harvested off the Eastern Shore. But local watermen will tell you that the ideal time to enjoy local oysters is in months that contain the letter R — and yes, that rules out the summer. For the juiciest, most succulent local oysters, do your shucking from September through April.


Local shops often hold off-season sales. After the busy summer season, many local shops are eager to clear out inventory to make room for new stock. That means special off-season sales, especially at the end of the year and during the annual spring Sidewalk Sale.


The weather may be better. Now, this may not hold true for, say, February, but shoulder season weather is indeed often superior to summer weather on the Eastern Shore. The summer heat can be extreme, particularly in July and August, and the mosquitos can be a nuisance as well. April, May, September, and October promise sunny days minus the heat and humidity of high summer.


You can take advantage of off-season rates. There are a limited number of beds available in Cape Charles, which means prices can be high in the peak season. Whether you’re staying in a local hotel, inn, or vacation rental, you can often shave a significant amount off of your nightly rate by planning your trip in the off-season.



What should you pack for a trip to Cape Charles? This isn’t your typical beach town, and your packing list should reflect that. Sure, you’ll need all your standard beach-going gear — swimsuits, flip-flops, beach towels, etc. — but there are a few more items you should pack that will help you make the most of your trip.

Before we get into our list, a quick note: Cape Charles is located in a fairly remote area on the tip of the Eastern Shore, but it’s not completely isolated. There’s a Food Lion and a Dollar Tree in town, plus a Walmart not too far up the road in Onley. And of course, it’s just a quick trip across the Chesapeake Bay Bridge-Tunnel to reach Hampton Roads, one of the biggest metro areas in the Southeast. In other words, if you forget something, it’s not a big deal.


Now that we’ve got that covered, let’s talk about a few not-so-basic items you should consider packing for your trip to Cape Charles.

  • Pool floats. With its location on the Chesapeake Bay, Cape Charles’ waters are calm and shallow — no monster waves here. That makes it the perfect place to kick back on a pool float to enjoy the gentle waves. It’s also perfect for kayaking and paddleboarding; bring your own or rent them once you arrive in town.
  • Walking/hiking shoes. If you’re visiting Cape Charles in the warmer months, you may think sandals are the only footwear you’ll need. And that’s fine if you’re planning to spend your entire visit on the beach. However, you should know that Cape Charles and its surrounds offer some excellent hiking trails. It’s also fun to simply take a long stroll around town.
  • Binoculars. Cape Charles and Virginia’s Eastern Shore are major destinations for serious birdwatchers [link to birdwatching blog post]. But you don’t have to be an expert to engage in some ornithology. Check out Birding Eastern Shore’s website to learn a bit about local species, then see what you can find at the beach or on local hiking trails.
  • Oyster knives, crab crackers, etc. If you’re planning to prepare some local seafood in your rental home (and you absolutely should!), make sure you have the proper supplies. While some properties may stock oyster knives, crab pots, and other necessities, you can’t always be sure they’ll be available to you. Whether you’re looking to shuck some local oysters or hold a crab boil in the backyard, it’s a good idea to pack what you’ll need just in case.
  • Telescope. If you have a telescope gathering dust in your attic, now’s the perfect time to brush it off and bring it with you. Cape Charles’ remote location makes it ideal for stargazing. Even if you don’t have a telescope, be sure to go outside and stare up at the stars at least once during your stay.


So you’ve visited Cape Charles, and suddenly you find yourself wanting to buy a home here. Don’t worry — it’s a common enough occurrence. The town tends to have that effect on people. Whether you’re a retiree, a young family, or somewhere in between, Cape Charles offers the chance to live a vacation lifestyle year-round. Luckily, there are homes available for every type of buyer. 

Buying a home in the Cape Charles historic district

Cape Charles’ historic district is a compact area mostly populated with homes built at the turn of the century. This is one of the more sought-after parts of Cape Charles for buyers thanks to its charm and walkability — residents can enjoy easy pedestrian access to the beach, Central Park, and downtown from anywhere in the historic district. The area is increasingly popular with second homeowners who may rent out their properties to vacation renters for extra income when they’re not staying there themselves. Homes range from tiny bungalows to sprawling Victorians to duplexes, offering a range of sizes for different types of buyers.

Buying a home in Bay Creek

Bay Creek isn’t just a resort with an incredible golf course. It’s also a thriving community that’s home to hundreds of residents. Set on over 1,700 pristine acres, Bay Creek boasts a large private beach and miles of hiking trails through a nature preserve. Homes here are new with a classic coastal aesthetic.

Homes in King’s Creek Landing and Beyond

Look beyond the historic district and Bay Creek to find some of the area’s best values. Developments like King’s Creek Landing offer newer homes within just a short drive of Cape Charles proper. You can also find nearby homes situated on the water, on farmland, or in neighboring communities like Cheriton, Eastville, and Oyster.

Ready to buy a home in Cape Charles? See our list of local realtors here [link to “Living in Cape Charles” page] to get started today.