Summer may be over, but that doesn’t mean you need to forgo getaways to coastal towns. In fact, thanks to fewer crowds, off-season deals, and family-friendly festivals, fall may be the best time for a coastal getaway. Grab a light jacket or sweater and let’s go!

1. Colonial Beach

Colonial Beach at Sunset
Photo Credit: Chris Militzer, @miliman12

Situated on Virginia’s Northern Neck, the charming four-block-wide town of Colonial Beach is known for golf carts, palm trees, and ospreys. It’s also home to a two-mile stretch of beachfront that is the second longest in Virginia. Stop in the Museum at Colonial Beach for the scoop on what was once called the “Playground on the Potomac,” then get your fill of presidential history at the George Washington Birthplace National Monument and James Monroe Birthplace Park & Museum. You’ll also want to make a few stops on the Chesapeake Bay Wine Trail, including Monroe Bay Winery and Ingleside Vineyards.

Where to Stay:

Where to Eat:

  • Dockside Restaurant & Tiki Bar
  • Wilkerson’s Seafood Restaurant
  • Circa 1892

2. Cape Charles

Cape Charles Natural Area Preserve
Photo Credit: Rachel Stevens

On the southernmost tip of Virginia's Eastern Shore is historic Cape Charles, a quiet, tree-lined village dotted with colorful Victorian-style homes, including several that were featured on HGTV’s Beachfront Bargain Hunt. This coastal hamlet is known for gentle waters, kid-friendly beaches, and dramatic sunsets over the Chesapeake Bay. Start your day with a “cuppa” at Cape Charles Coffee House, then stroll Main Street after lunch for ice cream scoops at the walk-up window at Brown Dog Ice Cream. At Kiptopeke State Park, rent a one- or two-person kayak for a paddle to crumbling ghost ships that date to World War II.

Where to Stay:

Where to Eat:

3. Chincoteague

Birds taking flight above a stream in Chincoteague National Wildlife Refuge
Photo Credit: Bill Crabtree Jr.

The wild, untamed ponies put Chincoteague on the map in 1961 with the movie Misty of Chincoteague. Stroll barefoot across the white-sand beaches of this unspoiled barrier island, then rent cruiser bikes at The Bike Depot to explore the island on two wheels. At Chincoteague National Wildlife Refuge, an easy hike leads to the red-and-white striped Assateague Lighthouse. Book a guided kayak tour or nature cruise across grassy marshes and coastal waterways with Assateague Explorer, which operates from April through October. Keep your eyes open for wild ponies, as well as egrets, eagles, and dolphins.

Where to Stay:

Where to Eat:

4. Virginia Beach

Virginia Beach Boardwalk

Virginia Beach wows visitors with its 38 miles of sandy beaches, state parks, historic attractions and colorful murals, like the “Greetings from Virginia Beach” mural at The Beach Bully on 19th Street. That’s not to mention its three-mile stretch of boardwalk, which runs from 2nd Street to 40th Street, affording coveted views across the Atlantic Ocean. Snap a selfie with the 34-foot-tall statue of King Neptune at 31st Street, then head to the horse corral at 26th Street for a one-hour guided horseback ride on the beach with Virginia Beach Horseback. At First Landing State Park, see curious bald cypress trees along the Bald Cypress Trail.

Where to Stay:

Where to Eat:

5. Sandbridge

Seagrass waving in the breeze in front of the ocean in Sandbridge, VA
Photo Credit: Brian Camp, @brian_k_camp

Sandbridge is the go-to destination among shore-goers eager to spend a quiet week in a vacation rental right on the beach. Thanks to off-season rates, it can be a less expensive rental, too. As a bonus, there’s free parking in all the municipal lots after Labor Day. Wildlife watchers will love Back Bay National Wildlife Refuge, which serves as an important stopover for more than 300 species of migratory birds heading south in the fall. From Back Bay, visitors can take the Blue Goose Tram to False Cape State Park for a ranger-guided exploration or to hike along some of the park’s nature trails, like the Marsh Ridge Trail.

Where to Stay:

Where to Eat:

6. Wachapreague

Wachapreague
Photo Credit: Adam Lewis, @adamtlewis

Located near the middle of Virginia’s Eastern Shore, Wachapreague is equidistant from Cape Charles and Chincoteague (both are roughly 45 minutes away by car), but this coastal town has a charm all its own. Wachapreague is noted for sport fishing, as well as picturesque views in fall thanks to changing foliage across a backdrop of marshes, wetlands and waterways. At the Eastern Shore of Virginia National Wildlife Refuge, enjoy an easy hike on the Butterfly Trail, which showcases a military history that dates to World War II when military were stationed here to protect the Chesapeake Bay.

Where to Stay:

Where to Eat:

7. Kilmarnock

Beaches of Hughlett Point Natural Area Preserve at sunrise in Kilmarnock

Kilmarnock is a charming coastal town on Virginia’s Northern Neck that delights with quaint antique shops, art galleries, and boutiques. It’s also close to several wineries and breweries with outdoor patios, including Good Luck Cellars and The Dog & Oyster Micro-Vineyard. Given its proximity to waterways, Kilmarnock is ideal for kayaking and boating, as well as fishing and crabbing. At Hughlett Point Natural Area Preserve, an easy loop hike guides visitors across a forest of loblolly pines and hardwoods before reaching sandy shores and overlooks for views across scenic wetlands and the Chesapeake Bay.  

Where to Stay:

Where to Eat:

8. Hampton

Fort Monroe
Photo Credit: Bill Crabtree Jr.

Hampton boasts sandy beaches, military attractions like Fort Monroe, history museums, and gorgeous green spaces like Sandy Bottom Nature Park, which offers miles of kid-friendly trails, as well as scenic wetlands, sparkling lakes, boat rentals, campsites, and a fishing pier. In October, the Phoebus Fall Festival boasts live music, food vendors, arts and crafts, and plenty of family-friendly activities. Kick off your shoes for a sandy stroll at Buckroe Beach or Grandview Nature Preserve, then take a tour of the Old Point Comfort Lighthouse where you can walk the grounds or enjoy a fair-weather picnic.

Where to Stay:

Where to Eat:

9. Mathews County

chesbayMathews

There are plenty of sandy shores on the Chesapeake Bay in Mathews County, including Haven Beach and Bethel Beach Natural Area Preserve. And oysters, of course; in November, plan to attend the Urbanna Oyster Festival. It’s the largest oyster festival in the U.S. and it’s a must for sampling raw, grilled, poached, and roasted oysters. You’ll also want to spectate the oyster shucking competition and the annual fireman’s parade. Public launch sites beckon visitors to drop in their kayaks and stand-up paddleboards to paddle out to remote beaches and marshlands, even the 58-foot-tall New Point Comfort Lighthouse.

Where to Stay:

Where to Eat:

10. Gloucester

Inn at Warner Hall in Gloucester
Photo Credit: Consociate Media, @consociatemedia

There is a lot for nature lovers in Gloucester, including Beaverdam Park, Gloucester Point Beach Park, and Machicomoco State Park, which has three hiking trails, car top boat launches, and a campground with tent and RV sites, as well as three yurts. Gloucester Main Street Village welcomes visitors with boutique shops like Goodman’s Interiors & Antiques and Up South, a clothing shop. Historic landmarks also beckon, such as Walter Reed Birthplace and the Rosewell Ruins, the site of a former colonial mansion that was destroyed by a fire in 1916.

Where to Stay:

Where to Eat: