15 Small Towns in Virginia for a Relaxing Weekend Getaway

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There are so many fantastic places to visit in Virginia. These are some of the best small towns in Virginia – ranging from small coastal towns to ones nestled in the mountains.

We have selected Virginia small towns that cover different areas of the state and they are all ones I have personally been to and truly loved! I have eaten seafood in Onancock and rode along the Virginia Creeper Trail in Abingdon.

Did we miss any cute towns in VA? Let us know in the comments! Thanks!

Best Small Towns in Virginia

Cape Charles

The small and charming Cape Charles is a town located on the Chesapeake Bay in Northampton County and was founded in 1884. It is on Virginia’s Eastern Shore.

It feels like you’re traveling back in time when you visit Cape Charles and you’ll be instantly transplanted back to the 1880s when the railroad and ferry industries were booming.

Cape Charles - best weekend trips from Richmond VA
Cape Charles

Cape Charles is teeming with many 19th-century, traditional homes and cottages… you can even rent one if you’re looking for accommodation in Cape Charles and stay in one right on the bay.

Aside from top-notch accommodation and serene views, there are several things to do in Cape Charles, such as visiting the Cape Charles Museum and Welcome Center where you can take in the history of the town, see historical engines, and more.

There are also golf courses, state parks, swimming, and many other opportunities nearby. Cape Charles is one of my favorite small towns in Virginia!

Chincoteague

Also located on Virginia’s Eastern Shore, Chincoteague is a fairly well-known town in VA but it is truly one of the rarest and coolest places in the state. A small port town, it is most famous for the Chincoteague National Wildlife Refuge… and wild ponies!

Assateague Island National Seashore, close to Chincoteague Island and shared with Maryland, is a fantastic place to experience undeveloped beaches and wild horses.

This area used to be super famous for its oyster industry and you can still find remnants of that today – be sure to visit the Museum of Chincoteague Island to learn more.

Wild Chincoteague Ponies of Assateague Island
Wild Chincoteague Ponies of Assateague Island

Some other things that make Chincoteague famous are the Assateague Lighthouse, one of the most beautiful lighthouses in Virginia as well as the Wallops Flight Facility Visitor’s Center.

There are also cozy cafes, restaurants, and much more.  You can find some great places to stay in Chincoteague for affordable prices, too. This is one of the best weekend getaways in Virginia.

Woodstock

Not to be confused with Woodstock, New York where the famous festival took place, Woodstock, Virginia is a charming small town in Virginia located in Shenandoah County.

While it is not as well-known as other towns in the area, it is located by the beautiful Shenandoah National Park and on the North Fork of the Shenandoah River.

Woodstock - best small towns in Virginia
Woodstock – best small towns in Virginia

One of the town’s main attractions is the Woodstock Museum of Shenandoah County where you can see exhibits dating back to the 18th-century. It is located in downtown Woodstock and is a can’t-miss place!

In addition, Woodstock has some of the best wineries near Shenandoah National Park! Be sure to check out North Mountain Vineyard and Winery to taste some delicious local wines.

If you’re into nature and hiking, be sure to head to Seven Bends State Park where you can walk the trails, kayak, and swim in the small lake.

Warrenton

Located in Fauquier County, the Virginia town of Warrenton is well-known as being the state’s ‘horse country. It hosted the first Virginia Gold Cup Race in 1922.

Warrenton was founded in 1810 and is known for being a great place for business – it is also home to several amazing cafes and restaurants.

One of the most famous places to visit in Warrenton is the 1959 statue of Chief Justice John Marshall which is located to the left of the old courthouse.

Warrenton
Warrenton

Another fantastic thing to do in Warrenton is to check out the historical 1808 Fauquier History Museum at the Old Jail, Brentmoor (the house of John Singleton Mosby – a Confederate military commander), and the Mediterranean Cellars where you can enjoy local wines and more!

Onancock

Another great place to visit on the Eastern Shore of Virginia is the small town of Onancock. This fishing town in Accomack County is located on the South Branch Onancock Creek and traces its roots back to 1680.

During the 1600s, John Smith named Onancock the ‘Gem of the Eastern Shore’ and it is known as a paradise for budget travelers these days.  You can also take several boat cruises from there and view the town’s historic buildings, churches, and more.

Another attraction in Onancock worth visiting is the Roseland Theater where you can watch a live show. The Eastern Shore of Virginia Historical Society is another place worth visiting if you’re curious about the area’s history.

If you’re into water sports, you can embark on some amazing kayaking adventures to Tobacco Island.

Abingdon

Located in Southwestern Virginia in Washington County, Abingdon is home to several historical landmarks and natural sights.

One of the most popular things to do in Abingdon is to visit the Martha Washington Inn & Spa that has been in operation since 1832 – you can stay there or simply take a tour of the place. The Barter Theatre is also another place worth checking out in the town. It boasts 160,000 + annual visitors and has been in operation since 1832.

Things to do in Abingdon Virginia
Abingdon

Some of the popular nature activities are to take a ride on one of Virginia’s most famous bike trails, the Virginia Creeper Trail. It is a rail-to-trail that passes through abandoned railroads from the 1970s, green forests, and more.

One of the most beautiful state parks in Virginia is Grayson Highlands State Park and it is also located nearby.  It has plenty of camping and hiking trails. Be sure to take a stroll on Abingdon’s historic Main Street, an 18th-century, 20-block historic district.

Abingdon is one of my favorite small towns in Virginia!

Farmville

Home to famous universities like Hampden-Sydney College and Longwood University, Farmville is located in Prince Edward and Cumberland Counties, only 65 miles away from the city of Richmond. It is one of the best day trips from Richmond!

The small, chilled-out town is also known for historical sites like High Bridge Trail State Park and Sailor’s Creek Battlefield Historical State Park where the last two battles of the Civil War took place.

Farmville
Farmville

It is also home to the R.R. Moton Museum, which is dedicated to the students from 1951 who went on strike in support of igniting Civil Rights.

It’s a great family vacation area where you can kayak in the lakes and rivers, go camping, golfing, zip-lining, fishing, hiking on nearby trails, and picnic in beautiful parks after exploring the town.

Kilmarnock

With a population of approximately 1,500 people, Kilmarnock is a small town located in Lancaster and Northumberland Counties in Virginia near the Rappahannock River.

The small Virginia town is also located near Westmoreland State Park and the birthplace of George Washington. Surprisingly, this area has a nice little wine scene!

Known for its serene atmosphere, the town has a quaint shopping and dining area downtown and during the 17th-century, the town was known as ‘The Crossroads’.

Kilmarnock
Kilmarnock

One of the most popular places to visit in Kilmarnock is the Kilmarnock Town Centre Park which has an open stage for concerts, an open-air gym, and colorful gardens.

Some other popular things to do in Kilmarnock are to visit the 18th-century Christ Church & Museum and the Lancaster Historical Society. You can also go hiking on the Hughlett Point Trail which is not too far from the beach and the town.

Leesburg

Founded in 1740, the town of Leesburg is located in Loudoun County and was, contrary to popular belief, was not named for the Confederate General of the same name. It is one of the most beautiful small towns in VA!

Leesburg is known for having a well-preserved and charming historical district downtown that has been included in the National Register of Historic Places since 1970.

Leesburg
Leesburg

There are plenty of significant (and fun) landmarks in Leesburg like the Shocktober Haunted House, Ida Lee Park Recreation Center, Stone Tower Winery, and the famous Ball’s Bluff Battlefield Regional Park.  This is one of the best small towns in Northern Virginia to pay a visit to!

Occoquan

Located in Prince William County, the town of Occoquan is a suburb of Washington DC and is located near Woodbridge. It is one of the cutest small towns in Virginia!

The name literally translates from Algonquian Doeg as ‘at the end of the water’ as it is situated along the Occoquan River. It has a deep-rooted Native history and has survived throughout the years despite fires, the Civil War, and more.

Occoquan
Occoquan

Today, the town of Occoquan is known for its historical center, ghost walks and historical tours, and its artistic community.

Some of the best things to do in Occoquan (and nearby) are to visit the River Mill Park, Mamie Davis Park, the free kayak launch ramp, Occoquan Regional Park, Fountainhead Regional Park, Mason Neck State Park, the Mill House Museum, and more.

Smithfield

A small town located in Isle of Wight County Virginia is Smithfield, Virginia. While people from out-of-state may not know Smithfield, they do know Virginia Ham or Smithfield Ham and that is one of the things that the town is famous for!

Smithfield was first colonized in 1634 and is situated just south of Jamestown and it sits on the Pagan River. The Natives called this land Warascoyak which meant ‘point of land’.

Smithfield
Smithfield

Some of the historical things to do in Smithfield are to visit Wharf Hill, the Mansion on Main, and St. Luke’s Church. And, of course, be sure to try out some of the famous Smithfield ham and peanuts when you visit!

Wytheville

One of southwestern Virginia’s more adorable towns is Wytheville, located in Wythe County.  Named after one of the signers of the Declaration of Independence, George Wythe, the town has just over 8,000 people and is known for being a crossroads for travelers.

Throughout the Civil War, Wytheville was attacked on multiple occasions. Some of the prominent sights in Wytheville are the Wythe County Poorhouse Farm, Wytheville Historic District, Haller-Gibboney Rock House, Crockett’s Cove Presbyterian Church, and more.

2 Nearby - High Rocks Trail in Wytheville
High Rocks Trail in Wytheville

In addition, the town of Wytheville is home to the Chautauqua Festival that is held annually every June.  It has been going on since 1985 and has live concerts, arts and crafts, hot air ballooning, and more. It is held at Elizabeth Brown Memorial Park.

Wytheville is one of the best weekend trips from Richmond and Charlotte and many other places!

Middleburg

Middleburg is a popular town in Virginia that is located in Loudoun County. It is small and has a population of merely 800 or so people. It was known traditionally as the US Horse and Hunt Capital as it played an active role in steeplechases, foxhunting, and had large estates.

In addition, the Middleburg Historic District, dating back to the 19th-century, is on the National Register of Historic Places.

Established in 1787, the town is extremely charming and one of the best ones to visit in the state. It even is home to the oldest inn in the US – the Red Fox Inn & Tavern (formerly known as Chinn’s Ordinary) which has been in operation since 1728.

Middleburg
Middleburg

Some other places that are worthy of visiting in Middleburg are the Green Pastures, Welbourne, Burrland Farm Historic District, the Mill House, and more.

Culpeper

Declared the ‘prettiest town in Virginia’ by Architectural Digest, the town of Culpeper surely deserves the title! It is the only incorporated town in Culpeper County and has a growing population and has since the 1980s when it was considered to be a ‘bedroom’ community for Northern Virginia and the DC area.

Culpeper
Culpeper

There are many things to do in Culpeper, such as visiting the National Audio-Visual Conservation Center, the downtown Culpeper Theatre, and more.

South Boston

Another fabulous town in Virginia is South Boston, located in south-central Virginia. Situated in Halifax County, it has around 8,000 residents and was, naturally, named for Boston, MA.

Some of the main attractions in South Boston are E.L. Evans House, Reedy Creek Site, South Boston Historic District, and more. The aforementioned sights are all listed on the National Register of Historic Places.

The Virginia town used to be home to the National Tobacco Festival but it was later moved to Richmond until 1984 when it stopped due to low interest and rising production costs. Until the Great Depression, the town of South Boston was the US’ second-largest tobacco producer.

What are the best small towns in Virginia that we missed on the list? Let us know in the comments! Thanks!

Pin this Virginia Small Towns Guide

Are you looking for the best small towns in Virginia for a quick weekend getaway? These Virginia small towns are cute, chilled out, and offer a lot to do! | Places to visit in Virginia | Things to do in Virginia | Small towns in VA | VA small towns | What to do in Virginia | Virginia hiking | Virginia beach towns | Virginia coastal towns | Things to do in Southwest Virginia | Virginia places to visit

Photo Credits:

Culpeper // Editorial credit: refrina / Shutterstock.com
Middleburg // Editorial credit: Nigel Jarvis / Shutterstock.com
Occoquan // Editorial credit: Malachi Jacobs / Shutterstock.com
Leesburg // Editorial credit: Michael Kaercher / Shutterstock.com
Farmville // Editorial credit: Lekali Studio / Shutterstock.com
Warrenton // Editorial credit: refrina / Shutterstock.com

16 thoughts on “15 Small Towns in Virginia for a Relaxing Weekend Getaway

  1. Julie says:

    Cool! Occoquan made the list! Read the brief and love how it mentioned our wonderful boat dock (which we don’t have) and every park NOT in Occoquan! LOL. No mention of our free kayak launch, all the shops, the Air BnBs, OUR park and its events, as well as our restaurants. SMH At least were on the list!

    • Megan Starr says:

      Thanks for the message, Julie! I tried listing stuff nearby but really should have focused more on Occoquan itself – so I changed that to include your parks and the kayak ramp as well! I didn’t want to list food there for now as I wanted to keep it quite generic and I haven’t been in years – but please let me know some of the best places to eat there so I include them on my upcoming lists when I visit home again! Thanks so much 🙂

      • Julie Richards says:

        Appreciate the amendment! We’re proud of our town and I’ll be happy to create a foodie list for you! 😊

        • Megan Starr says:

          Would absolutely love that! I was supposed to go home (currently in Germany) last year but then the pandemic happened – Occoquan was one of the places I wanted to return to when in VA actually! Thanks 🙂

  2. Stacie Lego says:

    Moved to Smithfield in 2013. A very nice small town with easy access to big town things. Only thing I am disappointed with is the restaurants. We’re pretty good when we first moved here but not much anymore.

    • Megan Starr says:

      Ah super interesting (and sad… I live for good food in a place). Fingers crossed it picks up soon!

  3. Hope Wright says:

    I’d sure love to see MORE nature adventures one hour/one and a half hours away from Virginia Beach! I know the Eastern Shore pretty well, FLSP, Back Bay, False Cape. I go aboard The Nature Bus. Thanks in advance!

  4. John R says:

    Leesburg was not named after Robert E Lee, but named earlier as noted below from Wikipedia source:

    Leesburg may have been named to honor the influential Thomas Lee or more generally for the Lee family. The name change was passed by an Act of Assembly in 1758. Francis Lightfoot Lee and Phillip Ludwell Lee, two of Thomas’ sons, were early town trustees. The town is not named, as is sometimes thought, for Robert E. Lee (Thomas’ great-grandnephew).

    • Sean says:

      John R thanks for clarifying. As a longtime resident of Leesburg I often hear people incorrectly say the town was named after the Confederate General but the truth is Robert E. Lee wasn’t even born yet when the town was first named Leesburg. This is a nice list of great places to visit but I would like to to see the author post a correction.

      • Megan Starr says:

        Thanks so much for the updated info! I am just now getting a chance to go through these comments and I have updated the post to state it was not actually named for him 🙂

    • Megan Starr says:

      Oh my gosh I don’t think I’ve ever been to Floyd! I know I’ve been to Floyd County but never the town! Need to head to Google right now and add it to my VA bucket list 😀 Thanks for the comment!

  5. Charles says:

    Abingdon and Wytheville, but what seems to be a common thing to do currently is skipping Marion, a town that also boasts incredible scenery and fun things to do.

    • Megan Starr says:

      Ah I totally forgot about Marion! I had a friend I went to university with that was from there and I went through one time but didn’t spend enough time there! I do remember the scenery though – need to make it back! Thanks for the comment!

  6. Mike says:

    A second vote for Floyd! We’re going back in a few weeks (from Ohio) after a 5-yr absence, and are really looking forward to it. If you love live music and friendly people, you’ve gotta go!

    • Megan Starr says:

      Ok I really feel like I am missing out… I guess I 100% need to make a trip there once I’m back in VA soon!

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