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Poolesville

Nestled in Montgomery County, Maryland, Poolesville is a charming small town surrounded by farmland and history, just a short drive from Washington, D.C. Rich in Civil War heritage, it blends agricultural roots with vibrant arts through community hubs like Locals Market, Calleva Farm, and Riverworks Art Center. The Crossvines winery on the local golf course supports winemakers and education, perfectly reflecting Poolesville’s blend of tradition, creativity, and community spirit.

From the Community

AFST

Featured Trip Itineraries

The Best Things To Do in Poolesville, Maryland

Recommendations

Landmark

John Poole House

The John Poole House, a charming 18th-century structure in Poolesville, MD, offers a glimpse into local history with its well-preserved architecture and captivating stories, making it a must-visit for history enthusiasts.

Landmark4.5/5

Historic Medley District Inc

Historic Medley District Inc in Poolesville is a charming blend of preserved heritage and vibrant local culture, offering visitors unique events, delightful shops, and a glimpse into the town's rich history.

Landmark4.8/5

Seneca Schoolhouse

Landmark4.2/5

Seneca Mill and Quarry Ruins

Outdoor4.7/5

Seneca Creek State Park

Welcome to Seneca Creek State Park! Enjoy hiking, biking, fishing, and boating along the picturesque Seneca Creek. Explore over 50 miles of trails, picnic areas, and a playground for the little ones. Keep an eye out for bald eagles and foxes! Don't forget your camera to capture the beauty of this outdoor oasis in Gaithersburg.

Landmark5/5

Seneca Historic District (Poolesville, Maryland)

Landmark4.3/5

Calleva

Landmark

Darnall Place

Landmark

Old Chiswell Place

Landmark4.8/5

East Oaks Farm

Landmark1/5

Walker Prehistoric Village Archeological Site

Outdoor4.7/5

L M Stevens Park

Landmark4.7/5

Riley's Lock (Lock 24)

Landmark4.6/5

Seneca Creek Aqueduct

Eat$$$4.4/5

Bassett's Restaurant

Eat$$$4.3/5

Cuginis Restaurant & Bar

Eat$$$4.4/5

Mexican Grill

Eat$$$4.3/5

The Crossvines

Nestled in the scenic countryside, The Crossvines offers a charming blend of exquisite wines and stunning vineyard views, making it a must-visit destination for wine lovers and nature enthusiasts alike.

Eat$$4.1/5

Kristophers Pizza

Eat$$4.3/5

House of Poolesville

Stays

Self Care$$$$4.45/5

Lansdowne Resort

Boasting a 45-hole golf course and a full-service spa, this Leesburg, Virginia resort is nestled in Washington DC’s wine country. The resort has a 5 pool aquatic centre and on-site fitness centre. Each guest room at the Lansdowne Resort features free Wi-Fi, a flat-screen cable TV, and gourmet coffee and coffee-making facilities. They are decorated in rich, warm tones and also offer plush terry bathrobes. Guests can enjoy spa and salon services at Spa Minerale or visit the tennis courts. Explore the hiking paths throughout the property and along the Potomac River. Four restaurants and lounges, including upscale fireside dining at Piedmont’s Table and light fare at Pub 46, are available at the Resort Lansdowne. The Leesburg Corner Premium Outlets are 6 miles away. Dry Mill Vineyard & Winery is 9 miles from the resort.

Stay$4.3/5

Hyatt Place Sterling/Dulles Airport-North

Featuring a 24-hour fitness centre and an outdoor pool, this hotel boasts free Wi-Fi and an on-site café. Dulles International Airport is 7 miles away. Rooms at Hyatt Place Sterling Dulles Airport North feature a flat-screen cable TV, a living area with sofa bed and an en suite bathroom with hairdryer. A mini-fridge, desk area and ironing facilities are included. At Hyatt North Place Sterling you will find a 24-hour reception, self-serve check in and express check out. A 24-hour in-room dining menu is available. Free parking is also offered. Cascades Marketplace Shopping Centre located 1 mile from the hotel offers a variety of outdoor shopping and dining options like Famous Dave’s Bar-B-Que. Leesburg Outlet is 16 minutes driving distance. Trump National Golf Club is 5 miles away.

Stay5/5

The Simon Suite, LLC

Nestled in scenic Barnesville, MD, The Simon Suite, LLC offers a unique blend of rustic charm and modern elegance, making it an ideal destination for intimate gatherings and unforgettable events. Experience its enchanting atmosphere and stunning surroundings.

Things To Do
Provided by

5/5

6 h

Private Loudoun County Wine Tour from DC with 3 Winery Stops

Let us escort you on a wonderful and relaxing full-day tour through some of the finest wineries in Loudoun County, Virginia. Complimentary hotel pick-up and drop-off is provided from all hotels within the Washington, DC metro area. Along the way, enjoy the natural beauty of the rural landscape on this scenic drive through Loudoun County. The tour includes stops at three popular local wineries, such as Stone Tower Winery, Fabbioli Cellars, and Casanel Vineyards (locations may vary depending on availability), with approximately one hour to enjoy at each destination. This is a private experience for groups of up to 14 passengers, with a total duration of six hours — time that will fly by as you ride in comfort and style in a luxury vehicle. Please note: Wine tastings and tours inside the wineries are not included. Customers are responsible for making their own reservations directly with the wineries. We provide transportation only.

$495.00

5/5

Washington DC Private Guided Bus Day Tour with Step Off Guide

Professional, passionate guides will lead a premium, private tour experience, including luxury transportation. Our guides will weave storytelling to enhance the visual experience. See the best of DC, what you want to see in 3-4 hours. A licensed guide will accompany you and step off and lead the way at the stops you pick. Embarking on a guided tour of Washington, DC promises a captivating journey through the heart of American history and culture. You can anticipate immersing yourself in iconic landmarks such as the majestic US Capitol Building where the nation's laws are crafted, and the White House, symbolizing the pinnacle of political power. The solemnity of the Lincoln Memorial, with its towering statue of the revered president, offers a moment of reflection of the nation's journey. A stroll along the National mall unveils a tapestry of monuments honoring heroes and events that shaped the nation including the Vietnam Veterans Memorial and the Martin Luther King Memorial.

$1,149.00

5/5

6 h

Northern Virginia Private Custom Wine Tour and Tasting from DC

Please note: This tour doesn't include admission for the Wineries. Price is for a 6 hour SUV transfer, additional fees will be charged if the tour exceeds 6 hours. This is a completely customizable private wine tour. The locations that are shown are just a sample. If you prefer to visit your desired wineries please let us know so we can customize your 6-hour tour accordingly. Some other sample itineraries include the following vineyards: 868 Estate Vineyards and Breaux Vineyards

$995.00

5/5

48 h

Private Two Days Trek from Marrakech to Berber Villages

This is a private Atlas trekking tour so it means nobody else will travel in your group. You will discover the high mountain in Morocco and north Africa on these two days by the climb in Mt Toubkal.

$160.34

5/5

Washington, DC Monumental Moonlight Private Guided Bus Tour

Your tour experience is illuminated in our Nation's Capital. Our professional step off tour guides lead you on a journey through memorials and historic landmarks that brighten at night. A licensed professional guide will accompany you and step off and lead the way at the stops you want to see the most. DC at night promises a captivating immersion into the city's rich history and iconic landmarks under the shimmering veil of darkness. As twilight descends, the majestic silhouette of the Capitol Building emerges, its dome illuminated against the night sky, symbolizing the heart of American democracy. The tour will navigate the National Mall, where the Lincoln Memorial stands solemnly, bathed in soft light, inviting reflection on the nation's ideals. Along the way the guide will recount tales of the city's past, weaving narratives of triumph, tragedy and resilience. History comes alive amidst the backdrop of illuminated monuments and landmarks.

$1,119.00

5/5

8 h

Gettysburg Private Trip and Guided Tour From the DC Area

Let us transport you in a luxury vehicle to a turning point in the Civil War. You will be escorted by a Battlefield guide that will tell an in depth narrative of those three fateful days in July 1863 This tour gives you an in depth narrative of the events of Gettysburg battle by showing you artifacts, cinematic perspective and actual battlefield settings from a licensed professional battlefield guide. Once you arrive at Gettysburg National Park, you will go to the Visitor Center where they will be expecting you. You will see an introductory film, the Cyclorama and their museum. Grab a quick bite before your tour. A licensed Battlefield guide will accompany you in the vehicle you arrived in and take you on a two hour tour around the Battlefield, 16 stops all together. You will have the opportunity to step out at many of these stops along the way. The driving portion of the tour is two hours.

$1,699.00

5/5

48 h

Philadelphia and New York City 2-Day Tour from Washington DC

See three of the East Coast’s biggest cities in two days on this small-group tour from Washington, D.C. Trace American history through Philadelphia, where the Liberty Bell and Independence Hall mark the birthplace of the nation, then head to New York for a guided run through the financial district, with Wall Street, the Charging Bull, Rockefeller Center, and the neon of Times Square, followed by a night tour that shows the city lit up after dark. The next day is yours to explore at your own pace, with optional skyline views at One World Trade Center, a Statue of Liberty cruise, and the aircraft-carrier museum of the U.S.S. Intrepid, plus the architectural Vessel and the floating Little Island park, before the return to Washington, D.C. A night’s hotel and round-trip transport are included.

$518.00

5/5

5 h

Colonial Annapolis and Naval Academy Half Day Private Bus Tour

Let us take you, and up to 12 of your friends, on an adventure through Navy culture and heritage. Historic Annapolis is Americas' sailing capital and home to the US Naval Academy, nestled along the Chesapeake region. We will help explore the sites, sounds and taste of "Nap Town". Annapolis has been rated as one of the most beautiful towns in America by Conde Nast Traveler. From historic buildings like the Maryland Statehouse to colonial homes and the vibrant downtown district of shops and restaurants, there's lots to love in Annapolis. Not to mention views of Chesapeake Bay and a stroll on the grounds of the Naval Academy.

$1,729.00

5/5

11 h

Colonial Williamsburg Private Vehicle Tour from the DC Area

Leaving from Washington DC to Virginia, after a couple of hours we will arrive at our destination where we will enjoy an in-depth historical rendering of Colonial Williamsburg which includes common sites and off-the-beaten-path visits. This guided tour of Colonia Williamsburg promises a captivating journey back in time, immersing visitors in the rich history and culture of America's colonial past. As travelers step into this meticulously preserved 18th century town, they are greeted by the sight of quaint cobblestone streets lined with authentic colonial buildings, bustling with costumed interpreters embodying characters from the era. Expect to stroll through the Governor's Palace adorned with period furnishings and lush gardens, and marvel at the craftsmanship of skilled artisans demonstrating traditional trades like blacksmithing and candle making. This tour offers a glimpse into the past, inviting guests to engage with history in a truly immersive and educational experience.

$4,069.00

5/5

Roatan Private Shore Excursion

Enjoy the comfort of your private vehicle with your loved ones and experience the west side of the island at your own pace. No waiting on other guest to join your tour before departing nor waiting on them to fill the bus to return to port or your vacation rental. You will visit some of the top sites for shopping, wildlife encounters, an optional stop to visit Roatan's popular West Bay Beach, admission rates vary and are not included. Many restaurants on site for you to dine and grab lunch if you do not wish to purchase a day pass. Loungers require a pass for access.

$550.00

5/5

8 h

Virginia Winery Excursion by Luxury Vehicle Three wineries

Let us take you through the beautiful Virginia countryside in a luxury vehicle as we introduce you various wineries of the old dominion state Nestled in the Northern Virginia heartland acres of vineyards sprinkled with wineries along country roads. We will drive you to a trio of distinct wineries that capture the essence of the mid-south

$1,379.00

5/5

5 h

Washington DC Presidential Memorials Experience Private Tour

Explore the presidential memorials of Washington, DC, each a testament to America's history and leadership. This guided tour offers a unique opportunity to reflect on the nation's journey through monumental neoclassical structures and modern contemplative spaces. An expert guide will provide in-depth insights into the history and symbolism of each memorial, enhancing your understanding of the American presidency. Enjoy a leisurely walk through the National Mall, taking in the beauty of these iconic sites while delving into their significance. - Discover the powerful stories behind each presidential memorial in DC - Guided tour with expert insights into American history and symbolism - Experience the stunning beauty of the National Mall - Perfect for history enthusiasts and those seeking a deeper understanding of America's leaders

$1,399.00

5/5

6 h

Harpers Ferry and Shepherdstown Private Tour

Enjoy a private, full-day historical adventure through West Virginia and Maryland with your own personal driver-guide. Visit the charming town of Harpers Ferry, the Bolivar Heights Battlefield, and the fascinating National Museum of Civil War Medicine. End your journey with a relaxing stroll along Carroll Creek Park in Frederick. Perfect for couples, families, or small groups who want a personalized, comfortable, and flexible travel experience filled with history, culture, and scenic beauty.

$999.00

5/5

Loudoun County 3-Winery Tour from DC Metro or Leesburg

Leave the route planning and driving to us on a relaxed day in Loudoun County wine country. Vineyard Voyages visits three wineries on one of our rotating scheduled routes, with convenient meeting points at West Falls Church Metro or Market Station in Leesburg. A Certified Tourism Ambassador guide hosts the experience while a professional driver handles the road, so you can focus on the scenery, wine, and time together. Each stop brings a different setting and personality, and the day is thoughtfully paced so you have time to taste, explore, and purchase lunch without organizing multiple cars or choosing a designated driver. Choose Explorer for transportation, your guide, and three winery visits while purchasing tastings as you go. Choose Connoisseur for the same hosted experience plus one pre-selected tasting or flight at each of the three wineries. Lunch and additional purchases are separate with both ticket types.

$119.99

5/5

1 h 20 mins

Historic Leesburg Guided Walking Tour

This is a guided walking tour of Leesburg’s fascinating historic district. Includes over a dozen attractons that illustrate the history and architecture of this quaint town. The tour is fun and enlightening! You'll see, for example, the site where Robert E. Lee planned the daring invasion of Maryland during the Civil War and the historic tavern where the the Mayor welcomed Gen. Marquis de Lafayette when he toured Leesburg in 1825, to name a few. The tour is about a mile of walking and lasts about 80 minutes. It's suitable for people of all ages.

$55.00

4.8/5

7 h

Leesburg Premium Outlets Shopping Tour

When the travel itinerary includes amazing shopping outings, Leesburg Premium Outlets is a must-see destination on the agenda. We have designed the perfect experience. Shopping at Virginia Premium Outlets is more convenient, they are exclusive shopping centers that do not have the problem of as much influx as those located within the city. Minimum 2 passengers.

$100.00

4.8/5

3 h

DC Daylight Tour™ Private Luxury Tour of Washington DC

See all the main sights in Washington DC with your private chauffeur aboard a late model SUV( Chevy Suburban or GMC Yukon). Maximum passengers 6. Please note that chauffeurs must stay with the vehicle at all times, but you can leave and explore the monuments on foot. Your chauffeur will wait nearby at the most convenient location. DCAcar's semi-narrated tours, conducted by professional chauffeurs cover all the main monuments in Washington, D.C. You can customize your 3-hour tour by selecting stops that interest your group. At the start, ask your chauffeur about must-see landmarks. Sample itinerary: (not in order) - The White House - Thomas Jefferson Memorial - Martin Luther King, Jr. Memorial - Lincoln Memorial/Korean War Veterans Memorial/Vietnam Veterans Memorial - National World War II Memorial - Washington Monument - United States Capitol Since this is a private tour you have the ability to skip or add other locations. Keep in mind that the tour cost is for 3 hours only.

$499.00

4.7/5

48 h

2-Day Niagara Falls Tour from D.C. w/ Overnight in the Falls Area

See Niagara Falls by day and by night on this two-day small-group trip from Washington, D.C. Drive north through the countryside to the falls, where you'll take in Horseshoe Falls, American Falls, and Bridal Veil Falls from a range of viewpoints. Add the optional Classic Tour for Whirlpool Park, the thundering Cave of the Winds, and the famous Maid of the Mist boat ride, then head out after dark for the illuminated night tour, when the falls glow under colored lights. The next day brings an optional stop at the world-renowned Corning Museum of Glass before the comfortable ride back to D.C. With a bilingual driver-guide and a night right at the falls, it's an unforgettable way to experience one of the world's great natural wonders.

$470.00

4.6/5

Mercedes Sprinter Van Day or Night Custom Tour of Washington DC

Looking for Washington DC private tours? Explore DC with World’s Five Star Limo Service. This Mercedes Van Tour is for up to 14 people. We provide pick up and drop off at any desired place in Washington DC, Virginia and Maryland. Distinguish customer service, modified limos and reliability shape our Tour Quality. Capture yourself in front of most of the historical buildings in the shortest possible time.

$790.00

4.6/5

1 h 15 mins

Montgomery Indoor Skydiving Experience with 2 Flights & Personalized Certificate

Feel the thrill of skydiving without jumping out of an airplane. It's true! Head to iFLY Montgomery, a premier indoor skydiving facility powered by a state-of-the-art vertical wind tunnel. After a training session, you'll experience free-fall conditions with the help of an instructor. No experience is necessary, and afterward, you can take home a personalized flight certificate.