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This Underrated Virginia County Has It All—Including Charming Hotels, Local Wineries, and the Newest State Park

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This Underrated Virginia County Has It All—Including Charming Hotels, Local Wineries, and the Newest State Park


Loudoun County, Virginia

  • Book a room at the newest addition to Leesburg’s hospitality scene, Hotel Burg, which opens to guests in August.

  • Visit one of the many wineries in the area—such as Breaux Vineyards in Purcellville or Good Spirit Farm Winery in Round Hill.

  • Browse vintage furniture and home decor at Lucketts Store in Leesburg.

  • Plan your trip to Loudoun County in the autumn, when the area’s fall foliage is on full display.

Virginia contains mountains, vineyards, small towns, luxury hotels, artistic hubs, and some of the most inspiring culinary scenes on the East Coast. While you could certainly traverse the Commonwealth to witness its multiplicity, you could also stick to one region—namely, Loudoun County.

Often referred to simply as “Loudoun,” Loudoun County is made up of a handful of towns and communities: Leesburg (the county seat), Middleburg, Purcellville, Waterford, Sterling, Round Hill, Lucketts, Hillsboro, Lovettsville, Hamilton, Ashburn, and Bluemont. “As a business owner in Loudoun, I really appreciate the diversity. Each city or town has its own vibe and culture. I also like how each city has its own local flair and events that the community can support,” says Silas Redd, owner of Nostalgia Boutique and Mister on Main in Purcellville.

“Some people ‘pit’ eastern Loudoun versus western Loudoun,” Jody Brady, founder and director of the Loudoun Appalachian Trail Festival, tells Travel + Leisure, explaining how eastern Loudoun is known for its suburban developments and shopping centers while western Loudoun has more farms and wineries. “But I think Loudoun works because east and west mix all this up and make the county the dynamic, thriving place it is,” she says. And as Reagan Walker, owner of Waterford Reservations, shares, “Whether you are into outdoor activities or culinary experiences, or you’re a wine or beer lover, there is truly something for everyone.”

Read on for our comprehensive guide to Loudoun County, Virginia.

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Best Hotels

Hotel Burg

Guest room inside Hotel Burg.

Hotel Burg

“Charming bed-and-breakfasts abound in Loudoun, and an array of hotels line the roads near Dulles International Airport, but the most recent talk of the town is the new, elegant Hotel Burg in the heart of Leesburg’s historic district,” says Brady. Set to open to guests this summer, the luxury boutique hotel will have a restaurant, The Huntōn, a cocktail bar, The Diana Lounge, and a rooftop bar.

Lansdowne Resort

“I have also loved visiting Lansdowne Resort. It is expansive, and the food is top-notch,” says Redd. The 500-acre, family-friendly property is located in Leesburg, and its amenities include three golf courses, a spa with 12 treatment rooms, and three outdoor pools.

Salamander Middleburg

“Of course, five-star Salamander Resort in Middleburg remains the top-tier stay in Loudoun,” says Brady. The resort is ideal for those travelers who enjoy balancing activities with relaxation. There’s horseback riding, golf, tennis, and a pool, plus a full-service spa to retreat to when you’re ready for some downtime.

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Best Things to Do

Amanda Andrade-Rhoades/For The Washington Post via Getty Images Hikers take in the view at Bear's Den Scenic Lookout.

Amanda Andrade-Rhoades/For The Washington Post via Getty Images

Hikers take in the view at Bear’s Den Scenic Lookout.

Go for a hike.

It’s not hard to find a way to stay active in Loudoun County, and one of the best ways to get in your steps and see the area is to hike. “Walk a stretch of the Appalachian Trail and picnic at the Bears Den Overlook, or explore the trails at Sweet Run State Park, Virginia’s newest state park,” says Brady.

Find some live music.

“We have so many talented local musicians, and you can’t beat the free summer music series in Hillsboro and Leesburg,” says Brady, who also recommends listening to music at Monk’s BBQ or Wheatland Spring. “Tarara Summer Concert Series is another favorite during the summer and early fall,” says Walker, describing “one of the most beautiful concert venues” she’s been to. “Invite your friends and family and enjoy a variety of great bands throughout the season.”

Visit a local winery, brewery, cidery, or distillery.

Places to grab a locally made drink abound in Loudoun County. Redd prefers Walsh Family Wine—and recommends a glass of their viognier—and Catoctin Creek Distillery, “for one of their highly curated ‘Dinner at the Distillery’ events.” Walker suggests checking out Breaux Vineyards, where you’re “surrounded by exquisite views of the vineyard,” and 8 Chains North. The latter, she notes, is dog-friendly and a “sure spot to stop if bringing your pup along.” Brady also has a few favorite spots, including Black Hoof Brewing Co. in Leesburg and Henway Hard Cider in Bluemont.

“In addition, most wineries and breweries have live local music and great food options on the weekends. Keep an eye out on their event calendars as most places host special events—festivals, wine dinners, and more,” says Walker.

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Attend a renowned tag sale.

Every year, thousands of shoppers make their way to Loudoun County to attend the Purcellville VA Tag Sale. “One of the largest events in Purcellville, this one-day event is a shopping and collectors’ dream! Our local boutiques have special discounts, and there are over 150 vendors selling antiques, handmade items, etc,” says Redd.

Towns to Visit

Gerville/Getty Images Aerial view of a Purcellville, Virginia residential area.

Gerville/Getty Images

Aerial view of a Purcellville, Virginia residential area.

Purcellville

“Purcellville is probably my favorite. It feels like it is one of the last small towns in Loudoun that hasn’t been overdeveloped. The community is really supportive of the restaurants, boutiques, and events,” says Redd.

Leesburg

“Downtown Leesburg has become such a fun place over the years, with so many wonderful restaurants, historic sites, shops, and live music,” says Walker. “The town also celebrates First Friday; the downtown is buzzing with people enjoying live music, art exhibits, open storefronts, food, and drink.”

Round Hill, Hillsboro, and Bluemont

“Round Hill, Hillsboro, and Bluemont are Loudoun’s three ‘A.T. Communities,’ a designation each town earned from the Appalachian Trail Conservancy for their commitment to the protection and promotion of the Appalachian Trail,” says Brady. “These three communities work together to put on the annual Loudoun A.T. Festival in June with a full day of Americana music, trail talks, nature crafts, and an art show.”

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Walker also adds that Hillsboro has an annual Independence Day celebration, which she describes as a “hometown experience full of life,” with “fireworks, live music, food, wine, beer, and kids’ fun.”

Waterford

“I might be biased because I grew up in the town and now live two miles outside of it, but there is something magical about Waterford,” says Walker. “It is filled with history, beautiful historic homes, and hosts the Waterford Fair annually. There is a lovely walking trail called the Phillips Farm Trail, which is a walk along the Catoctin Creek adjacent to the town.”

Middleburg

There’s no shortage of charm in Middleburg, a small town where equestrian heritage and storied history are on display around every corner. It’s also home to several luxe hotels and inns; along with Salamander Middleburg, there’s The Red Fox Inn & Tavern as well as Goodstone Inn & Restaurant.

Best Restaurants

The Conche Interior shot of The Conche dining room.

The Conche

Interior shot of The Conche dining room.

Purcellville

“Magnolias at the Mill has always been a top choice of mine. Whether I’m celebrating a special occasion, meeting my girlfriends for brunch, or simply stopping in for a nice lunch or dinner, the experience is always top-notch,” says Walker. For what Redd calls the “best BLT sandwich ever,” head to Market Burger Fries & Shakes. If you want a “great home-cooked breakfast,” he suggests Purcellville Family Restaurant.

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Leesburg

Walker calls EagleTree Farm Winery & Restaurants a “hidden gem.” “Located outside of Leesburg, they offer a delicious seasonal menu with excellent service,” she says. While in Leesburg, stop by any one of Brady’s favorites: Tuscarora Mill, SideBar, Shoe’s Cup and Cork, or The Conche.

Hillsboro

“I am a pizza lover, so one of my favorite stops is in the town of Hillsboro at Market in The Gap,” says Walker. She shares it “has amazing wood-fired pizza made right in front of you,” a “smaller cozy atmosphere inside,” and “an outdoor area for seating in warmer weather.”

Middleburg

If you find yourself in Middleburg, there are two iconic restaurants that come recommended by Brady. For the more traditional route, make a reservation at the Red Fox Inn & Tavern. In the mood for something more casual? King St. Oyster Bar, with its seafood entrees and happy hour specials, should do the trick.

Best Shopping

JackF/Adobe Stock Variety of assortments in store of antique furniture.

JackF/Adobe Stock

Variety of assortments in store of antique furniture.

Leesburg

“I am very into design and decor, so I absolutely love going to the Lucketts Store. They have so many amazing finds. I could literally spend all day there and will always find something to take home,” says Walker. “Leesburg boutiques make for a wonderful afternoon of shopping, including Muz & Roz, wldwst, Misguided Angels, Birch Tree Bookstore, Brick & Mortar Mercantile, and Madisonbelle,” adds Brady.

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Waterford

“I love The Corner Store in Waterford. Pop in and explore amazing vintage furniture and locally produced and handmade goods,” says Walker. “The store also has an excellent small menu created by Chef Estelle Richer-Legault. The freshness of the menu and experience are exceptional.”

Purcellville

“I like to score second-hand treasures in Purcellville at Nostalgia, Twigs, It’s Bazaar, and Re-Love It,” says Brady. Redd is also a fan of Twigs. “This place is the queen of unique gifts! Everything from jewelry and candles and soaps to tabletop books and womens wear,” he says, adding that Twin Flame Vintage, a “kitschy boutique focusing on vintage clothing, housewares, home decor, and ephemera,” is another one that travelers should have on their list. If it’s menswear you’re after, take a peek at Redd’s Mister on Main boutique housed inside its sibling store, Nostalgia.

Round Hill

“Elsass in Round Hill is one of my favorites,” says Redd. “It’s a former mechanic shop converted into an antique store specializing in French antiquities.” Elsass is open from Friday through Sunday or by appointment.

Lovettsville

According to Walker, the “best goat cheese around” can be found at Georges Mill Farm Artisan Cheese in Lovettsville. Long Stone Farm is also on her shortlist; bring a cooler so you can keep the pork, eggs, and other perishable products you pick up cold.

Best Time to Visit

LindasPhotography/Getty Images Autumn leaves in Loudoun County.

LindasPhotography/Getty Images

Autumn leaves in Loudoun County.

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“Fall is hands-down the best time to visit,” says Redd. “There’s nothing better than enjoying a local glass of wine and seeing the seasons change from the leaves on the trees and native plants.” Alternatively, says Brady, if you explore Loudoun in the spring, you may get to see the wildflowers at Balls Bluff or attend Loudoun Wildlife Conservancy’s Spring Native Plant Sale and the Leesburg Flower & Garden Festival in April. Walker, on the other hand, recommends planning your visit for late summer: “The backdrop is so beautiful this time of year. If you visit wineries, the vines are so lush and beautiful,” she says.

How to Get There

If you plan on flying to Loudoun, you’ll want to choose Dulles International Airport (IAD) as your destination. From there, you can either rent a car or book a taxi or rideshare service. IAD is only about a 20-to-40-minute drive away from Loudoun, depending on where you’re going within the county. There’s also the option to come by train from D.C. There are three Metrorail Silver Line stations that serve Loudoun: Dulles International Airport, Loudoun Gateway, and Ashburn Station.

How to Get Around

The most convenient way to explore Loudoun County is by car. This allows you the freedom to visit the different towns that make up the county, popping into different restaurants, shops, and wineries. Just be sure to assign a designated driver ahead of time if you plan on indulging in any wine or other alcoholic beverages.

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Va. governor concerned redistricting battle could make voters reluctant to cast ballot this fall – WTOP News

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Va. governor concerned redistricting battle could make voters reluctant to cast ballot this fall – WTOP News


Days after Virginia Democrats filed an emergency appeal with the U.S. Supreme Court as part of their ongoing redistricting battle, Gov. Abigail Spanberger said she’s focused on the fall midterm elections and ensuring voters are motivated to turn out.

Days after Virginia Democrats filed an emergency appeal with the U.S. Supreme Court as part of their ongoing redistricting battle, Gov. Abigail Spanberger said she’s focused on the fall midterm elections and ensuring voters are motivated to turn out.

After a bill signing at Inova Schar Cancer Institute on Wednesday, Spanberger made her most extensive public comments about the state’s redistricting plan. She cited the state’s May 12 deadline for any map changes, and said as a result, this year’s elections will proceed under the current map.

Spanberger’s remarks came a few days after Virginia’s Supreme Court struck down the Democrat-led redistricting push. Primaries in the state are scheduled for Aug. 4, with the November general election to follow.

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“What needs to happen is we need to focus on the task at hand, which is winning races in November,” Spanberger said.

“I believe, somewhat doggedly, that we will win two to four seats in the House of Representatives. … That is my goal. That is what I know is possible.”

The map Democrats proposed, experts said, could have resulted in a 10-1 Democratic majority representing Virginia in the U.S. House. But Republicans challenged the process Democrats in the General Assembly used to put the constitutional amendment before voters.

In a 4-3 opinion issued Friday morning, Virginia’s Supreme Court sided with the Republican challengers.

U.S. Supreme Court Chief Justice John Roberts gave Republicans until Thursday evening to respond to Democrats’ request for the emergency appeal.

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Spanberger defended the process the General Assembly used, adding: “I think I certainly would have wanted to, and did want to, see a different outcome with the Supreme Court ruling.”

Over three million people participated in the rare April special election, and Spanberger said she’s concerned those voters “have had the experience of casting a ballot in an election that was very important to them, including those on both sides of the referendum vote, only to have it be overturned, essentially, by the Supreme Court of Virginia.”

Elected officials, she said, will have to work to ensure “that people know that their votes do matter, and that when it comes to the ballot they’re going to cast — whether it’s for a primary over the summer or for the general election into the fall — that they shouldn’t feel depleted or defeated, that their votes matter.”

Spanberger called the appeal to the U.S. Supreme Court “important, but when it comes to the execution of elections, no matter the outcome in that case, we will be running our elections beginning next month with early voting on the current maps that we have.”

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What does ‘election’ mean? One answer doomed Virginia’s new congressional map | CNN

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What does ‘election’ mean? One answer doomed Virginia’s new congressional map | CNN


Virginia’s Supreme Court dealt a blow to Democrats last week in the tit-for-tat redistricting war playing out ahead of the midterms.

In a 4-3 ruling, justices nullified a new congressional map that could have given the Democrats four additional seats in the House of Representatives. Their argument centered on whether state lawmakers had followed proper procedure when they put a constitutional amendment on the ballot to allow for the redistricting. The procedural question hinged on a linguistic technicality: What constitutes an “election”?

EDITOR’S NOTE:  CNN’s “Word of the Week” brings you the meaning behind the words in the news.

Traditionally — and in Virginia’s case, under the requirements of the state constitution — states have redrawn their congressional districts every 10 years, when a new census comes out and the 435 members of the House are reapportioned according to the states’ new shares of the population. But President Donald Trump, facing dismal polls and the risk of losing his party’s already tenuous House majority, has urged Republican-controlled states to launch an aggressive mid-decade round of redistricting, in the hopes of gerrymandering Democratic seats off the map.

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Democratic-controlled states like California and Virginia have set out to draw gerrymanders of their own, aiming to wipe out Republican seats. Virginia voters, in a referendum last month, agreed to amend the state constitution to “temporarily adopt new congressional districts to restore fairness in the upcoming elections,” then to revert to the old rules after 2030.

That vote was meant to be the final part of the multistep process for amending the Virginia constitution. Before an amendment can go to a public referendum, it needs to be approved by the state legislature on two separate occasions: once before “the next general election,” and again after that election, under the newly chosen legislature.

The previous Virginia legislature passed the amendment on October 31, 2025. Election Day followed on November 4. The newly elected legislature then re-passed the amendment on January 16, 2026, to send it to the voters on April 21.

But four Virginia Supreme Court judges, three of them confirmed under Republican-controlled legislatures, ruled that the April voting was invalid. Although two successive legislatures had approved the amendment, the court argued that the first vote, back in October, had come too late — rather than voting before the election, as the constitutional timetable required, the legislature had voted after the 2025 general election was already happening.

In doing so, the court defined the “election” as having come into existence when early voting commenced on September 19, and not as merely taking place on Election Day. By the time Virginia’s General Assembly approved the amendment on October 31, the court argued, more than 1.3 million Virginians had already cast their ballots and therefore could not use their votes to express their approval or disapproval of the proposal.

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“The definition of ‘election’ has always broadly denoted the ‘act of choosing,’” Justice D. Arthur Kelsey wrote in the majority opinion.

Citing early dictionaries from lexicographers Samuel Johnson and Noah Webster, as well as legal dictionaries such as Black’s Law Dictionary, Kelsey devoted several pages of the opinion to parsing the meaning of an “election.” He argued that average citizens who cast their ballots early would likely understand themselves to be voting in the election. “This lexical sense of the noun ‘election’ must be distinguished from the noun phrase ‘election day,’” he wrote.

He continued, “The metes and bounds of an election begin with the point of casting votes and end with the point of receiving votes and closing the polls on the last day of the election. Election Day is the boundary marker for the last act constituting an election.”

The minority took issue with this definition. An election, the justices on the losing side countered, is the event that happens on Election Day.

“By focusing on the legislative history, dictionary definitions, and how legal scholars might interpret the term ‘election,’” Chief Justice Cleo Powell wrote in dissent, “The majority fails to apply the most basic tenet of interpretation of constitutional provisions: looking to the language of the constitution itself.”

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Powell argued that the majority’s definition of “election” contradicts how the word is defined in state and federal law. She cited a provision of Virginia’s constitution that states that the members of the House of Delegates “shall be elected … on the Tuesday succeeding the first Monday in November.” She also cited the Virginia code, which indicates that a “general election” is “an election held in the Commonwealth on the Tuesday after the first Monday in November.”

To make its point, the dissent ventured into metaphysical considerations about the mechanics of time. Treating the early voting period as part of the election would create a “causality paradox,” the dissent argued. “An election is a process that begins with early voting, but early voting must precede an election by forty-five days,” Powell wrote. “The majority’s definition creates an infinite voting loop that appears to have no established beginning, only a definitive end: Election Day.”

The dissent argued that the majority’s definition of “election” poses other conundrums as well: For example, Virginia law stipulates that voters can’t be compelled to attend trials during the time of an election. Does this mean that the courts are effectively hamstrung for several weeks from the start of early voting to Election Day?

By some assessments, both sides made reasonable and solidly sourced arguments. But the degree to which they fixated on the definition of “election” seemed to strike at least one analyst as pedantic. Vox’s Ian Millhiser put it this way: “Rather than producing two eye-glazing opinions fighting over the meaning of a word whose definition appears to shift depending on both linguistic and historical context, the justices would have produced a better opinion if they had asked a more basic question: What is the relevant provision of the Virginia Constitution actually supposed to accomplish?”

That more basic question is, in some ways, harder to answer.

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The court’s majority wrote that the laborious process of amending the constitution gives voters both an indirect and a direct opportunity to voice their views on a proposed change, voting for or against the legislators who initially approve an amendment, and then voting on the amendment itself. But if the justices were concerned about the will of the 1.3 million early voters who cast their ballots before the legislators approved the redistricting amendment, they seemed to gloss over the more than 1.6 million Virginians who voted in favor of the new maps, says Carolyn Fiddler, a Virginia state politics expert who has previously worked for Democratic and progressive organizations.

“How can they say that voters didn’t have a say?” she says. “Voters had a say and a clear majority.”

The text of Virginia’s Constitution doesn’t expand on why the constitutional amendment process is structured the way it is. But what it doesn’t say is illuminating, says Quinn Yeargain, a law professor at Michigan State University. Virginia’s previous constitution, from 1902, specified that the legislature must publicize a proposed amendment to voters three months before the intervening election. When the constitution was revised in 1971, that requirement was omitted.

“So they effectively made it easier, then, to amend the constitution,” Yeargain says. “At that point, they knew exactly how to use the words to achieve the kind of thing the majority said that it was trying to achieve. And they took those words out.”

Democratic officials in Virginia have asked the US Supreme Court to reinstate the new map for the midterms, though the emergency appeal is unlikely to succeed.

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The Virginia Supreme Court ruling, with its insistence that an election begins at the first opportunity for balloting, stands in apparent contrast to other redistricting decisions. After the Supreme Court’s Voting Rights Act decision in Louisiana v. Callais made it harder for voters of color to challenge redistricting plans as discriminatory, Southern states have scrambled to redraw their congressional maps in ways that favor the GOP — in some cases, after early votes in primary elections had already been counted. The new maps will make this year’s House elections the least competitive on record, the journalist G. Elliott Morris wrote in his Substack newsletter Strength In Numbers.

The current redistricting war makes for a “deeply dissatisfying situation from beginning to end,” Yeargain says. On its own, Yeargain says he doesn’t much care for Virginia’s proposed redistricting amendment, but the nationwide struggle goes beyond the individual merits of each state’s plans.

“Instead, we’re asking a broader question,” he says. “And that is whether this year’s congressional elections are going to be legitimate in some form or another.”

What is an “election,” exactly? Virginia’s Supreme Court majority sought an answer in dictionaries, which define the word as the act or process of choosing. But who is doing the choosing? As Republicans aggressively redraw electoral maps at the behest of the president, and as Democrats attempt to counterbalance those efforts with their own redistricting, it appears that a more consequential election — one in which politicians choose their voters — is already well underway.

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Headlines from across the state: Virginia becomes first Southern state to mandate paid family and medical leave for workers; more …

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Headlines from across the state: Virginia becomes first Southern state to mandate paid family and medical leave for workers; more …


Here are some of the top headlines from other news outlets around Virginia. Some content may be behind a metered paywall:

Politics:

Virginia becomes first Southern state to mandate paid family and medical leave for workers. — Virginia Mercury.

Local:

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Former Richmond Free Press building sold to apartment developer for $2 million. — Richmond Times-Dispatch (paywall).

Cavalier Hotel property could be sold to real estate investment firm. — The (Norfolk) Virginian-Pilot (paywall).

Richmond judges take legal action against city government over courthouse conditions. — The Richmonder.

Sports:

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Ex-Virginia Tech basketball coach Johnson agrees to become Ferrum coach. — The Roanoke Times (paywall).

Weather:

For more weather news, follow weather journalist Kevin Myatt on Twitter / X at @kevinmyattwx and sign up for his free weather email newsletter. His weekly column appears in Cardinal News each Wednesday afternoon.

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