2 Weeks Traveling Virginia by Train – Itinerary

Follow along as I travel through Virginia on Amtrak’s Northeast Regional train with stops in Hampton, Williamsburg, Fredericksburg, Ashland, and Prince William County. I’ll travel for two weeks researching several articles including Amazing Virginia Foods and Where to Find Them for Travel Awaits, Best Virginia Wineries for Chilled Magazine, a Hampton Getaway for Bass Angler Magazine, and Virginia by Train for Evolving Magazine. In addition, I’ll be gathering information for one-day itineraries in each city to include in a future train guide.

3 Days in Hampton, VA

Lodging: Check in at Hampton Inn Hampton-Newport News

Day 1 – Hampton

Tour the Hampton History Museum.

Hampton History Museum recounts the history of America’s oldest, continuous English-founded settlement from its inhabitance by the Kecoughtan Indians to its role as the original home of NASA and the U.S. space program.

Walk directly out the back door of the Hampton History Museum to St. John’s Church, the oldest continuous English-founded parish in the U.S.

Lunch at The Grey Goose.

The Grey Goose, a long-time, downtown eatery, is known for their baked goods and their popular “Dinnertainment” shows.


Walk/drive to Hampton University Museum.            

Tour Hampton University Museum.

The Hampton Normal and Agricultural Institute, now Hampton University, opened its doors in 1868 under founder General Samuel Chapman Armstrong. The institution educated freedmen and later Native Americans. Under the forty-year term of the current university president, William R. Harvey, Hampton University is now among the top private universities in our nation.

While at Hampton University, we’ll visit the Emancipation Oak, site of the first Southern reading of the Emancipation Proclamation.

Head to Queens Way for dinner at Brown Chicken Brown Cow, a hip, downtown spot for burgers and barbecue. Queens Way is home to the Downtown Hampton Block Party, Hampton’s signature summer Saturday night event series.

Day 2 – Hampton

Walk to the Hampton Maritime Center to check-in for your cruise on the Miss Hampton II.

Board the Miss Hampton II a double-decked tour boat that offers daily narrated cruises of the Hampton Roads harbor and Chesapeake Bay. We’ll see local fishing boats, mighty commercial cargo ships, Blackbeard’s Point, Old Point Comfort, and the awesome gray fleet at the world’s largest naval instillation, the Norfolk Naval Base.


Be sure to wear comfortable shoes for a walking tour of Fort Wool, a fortification on which construction began in 1819. Fort Wool is located on a man-made island in the Hampton Roads harbor and is only accessible by boat. 

Take a guided tour of the Virginia Air & Space Center.

The Virginia Air & Space Center, the official visitor center for NASA Langley Research Center, features over 100 hands-on exhibits. Imagine life in humanity’s future space colonies as you enter the Inflatable Lunar Habitat, one of the center’s newest exhibits, which is the first of its kind to be open to the public at a NASA Visitor Center. Discover the new Be an Astronaut exhibit, a hands-on, multi-step simulation of space missions. Elsewhere in the center you’ll find several suspended, full-size aircraft, and a 3-D IMAX Theater.

Go for a spin on The Hampton Carousel. Built in 1920, the carousel is completely restored to its original beauty and housed in its own weather-protected pavilion on the city’s downtown waterfront. It is one of only 70 antique wooden merry-go-rounds still operating in the United States. The carousel is open year-round.

Dinner at Mango Mangeaux.

Experience the charming neighborhood of Phoebus at Mango Mangeaux. The restaurant owners entered the limelight as contestants on ABC’s SharkTank when trying to find a partner for their Mango Mangeaux preserves product. Though they didn’t reel in a deal with a shark, they did catch thousands of new customers for their preserves, which can be enjoyed in many of the dishes at their restaurant.  

Day 3 – Hampton

A quick drive back through Phoebus takes us to Buckroe Beach. This former resort area is now a public park that features watersport rentals, party pavilions and a fishing pier.

Lunch at Hampton’s premier farm-to-table restaurant, The Point, serves seafood and Southern favorites in the quaint Phoebus neighborhood. Known for its antique and second-hand stores as well as multiple independent restaurants, Phoebus is home to Sly Clyde Ciderworks and The American Theatre


Tour the Casemate Museum at Fort Monroe, one of our nation’s newest national monuments.

On this site Fort Algernoune was built in 1609. This early fort served as a lookout and protector of the Jamestown Settlement and Hampton Roads harbor. We’ll see the shore where the first Africans who lived in the Virginia colony arrived at Hampton.  In 1619, a vessel carrying “twenty-odd” Angolan passengers arrived at Old Point Comfort near the point of land on which John Smith and crew arrived in 1607.  This historic landing marks the first step towards enslavement in the Virginia colony.

Fort Monroe was constructed from 1819-1834. During the Civil War, Fort Monroe was a Union-held bastion in the Confederate South. The fortress served as a safe-haven for men, women and children escaping enslavement after Union Major General Benjamin F. Butler declared the runaways “contraband of war” and refused to return them to their Confederate owners. The fort’s Casemate Museum houses the cell in which Confederate president Jefferson Davis was imprisoned following the Civil War. The fortress is also home to the Old Point Comfort Lighthouse.

Segway tour of historic Fort Monroe with Patriot Tours and Provisions.

Discover history via cutting-edge conveyance. This one-hour “Breeze” tour takes riders through the inner fort and down to the waterfront. Our guide will point out sites of historical significance as we roll along.

Driving tour of outlying Fort Monroe and Buckroe Beach.

Since it was decommissioned in 2011, Fort Monroe has become home to a host of businesses and recreational spots. On our tour we’ll see The Chamberlin, Paradise Ocean Club and Oozlefinch Craft Brewery

In addition to the tour, we will learn about the new Fort Monroe Visitor & Education Center. This new asset to Fort Monroe will interpret the history of Fort Monroe from its first Native inhabitants to the first African arrival, the Civil War and beyond.

Dinner at The Deadrise , the Old Point Comfort Marina restaurant. Enjoy unrivaled views of Hampton Roads from Hampton’s top fresh-catch restaurant.50394028_2242858975983665_7087069975432658944_o.jpg

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1 Day in Williamsburg

Lodging: Check in at Patrick Henry Inn


While seafood is indeed a Virginian specialty, visitors can still easily find a variety of different restaurants and cuisines while in Williamsburg. Much of the produce and food is regionally-sourced, so guests may often rest assured that each meal is homegrown. Many restaurants also offer vegetarian dishes, so there’s something for every palate in Williamsburg.


  • Williamsburg Winery
  • Enjoy Colonial Williamsburg – Travel back in time and immerse yourself in an 18th-century city. Explore historic buildings and wander through gardens. Engage our nation’s founders and gain a new perspective on our American story. Guests of all ages can meet the nation’s founders, enjoy period stories, and even try their hands at historic trades and games, with a focus on fun for young revolutionaries.
  • Jamestown Settlement – Ever wonder what Pocahontas’ childhood was really like? Here’s your chance to tour a re-created Powhatan Indian village and take part in activities Pocahontas herself would have helped with as a child, like grinding corn and making cordage. You can also learn about the convergence of Powhatan Indian, English and African cultures in 1607:A Nation Takes Root, a docudrama film that chronicles Jamestown’s origins in England and the colonists’ struggle to survive and thrive in Virginia. Don’t miss the yearlong special exhibition, “TENACITY: Women in Jamestown and Early Virginia.” Board re-creations of the three ships that transported the original Jamestown colonists to Virginia in 1607. Tour a re-created 1610-1614 colonial fort to experience its military and commercial character.

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2 Days in Ashland/Richmond

Lodging: Check in at Henry Clay Inn

We invite you to step into the warmth, charm, and hospitality of The Henry Clay Inn®. Our Georgian-style Inn is a centerpiece in historic Ashland, VA, “The Center of the Universe!” Enjoy the warm welcome of our lobby with a gorgeous fireplace and sitting area and our Drawing Room with its own fireplace, perfect for your next event or meeting. The Drawing Room opens onto our spacious porch for sitting back and enjoying the sights and sounds of Ashland and is particularly popular with our train fans. Our cozy breakfast area provides the perfect spot to enjoy our newly re-opened kitchen for full breakfast or just sip a cup of tea or coffee and read the morning paper. The majority of our guest rooms are on our second floor, which also features a parlor with fireplace and is the ideal gathering spot for good conversation or to curl up with a good book and opens onto a lovely second-floor porch. Our selection of 13 rooms offers a variety of choices for your overnight stay and all feature private baths.


Day 1 – Ashland

Walk around Ashland 

The Town of Ashland is located 15 miles north of Richmond on I-95. Affectionately known as the “Center of the Universe”, Ashland offers lots of fun and interesting places to visit. The Visitor Center is housed in the Ashland Rail Station that was built in 1923. 

Whether your interests are trains, historic sites, or the thrills of nearby amusement park Kings Dominion, Ashland and Hanover County have something for everyone. Come and enjoy our small town hospitality!

Day 2 – Richmond

Uber to Richmond, Carytown to discover nine blocks of cute shops and independent restaurants. 

Richmond Beer Trail map

3 Days in Fredericksburg

*The Jasper – NEW cocktail bar (in Carytown, not Scott’s Addition): www.jasperbarrva.com  

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2 Days in Fredericksburg

Lodging: Check in at Courtyard by Marriott Fredericksburg Historic DistricM

Day 1 – Fredericksburg       

Start your day at Hyperion Espresso, a quaint corner coffee shop with outdoor seating, espresso drinks, pastries & packaged snacks.

Lodging: Check in at the Courtyard Fredericksburg Historic District.

Day 1 – Fredericksburg

Learn about the fascinating history of the area by visiting key sites such as Hugh Mercer Apothecary, Kenmore (home of George Washington’s sister, Betty), Mary Washington House (home of George Washington’s mother), Rising Sun Tavern and more. *All are within walking distances from hotel.

Take a quick ride to A. Smith Bowman Distillery for a tour of the facility and taste their hand-crafted spirits.

Enjoy a dinner at Kybecca, known for its small plates, craft cocktails, and decadent desserts.

Day 2 – Fredericksburg

Start your day at Eileen’s Bakery and Café for a morning treat. All pastries and breads are handmade fresh daily.

Hop on the trolley tour to explore historic downtown Fredericksburg. Tours start at the Fredericksburg Visitor Center.

Dine at FoodE, a farm-to-table restaurant in a former bank building. Chef Joy Crump was a contestant on Bravo’s “Top Chef” and owns another eatery downtown, Mercantile.

Arrive at Ferry Farm for a guided tour of the property. Ferry Farm is where George Washington lived from the age of 6 until he was 20.    

Stop by Goolrick’s Modern Pharmacy, one of the oldest continuously-operating soda fountains in America, for a malt, milkshake, fresh squeezed lemonade or cherry coke.

Mosey over to Orofino for a traditional Italian dinner. Make sure to save room for dessert – the tiramisu is out of this world! 

Day 3 – Fredericksburg

Start your day atAgora Downtown Coffee Shop, a local coffee shop that also functions as a used bookstore and gift shop.

Pack your own picnic for your train ride home with items from Old Town Butcher.

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2 Days in Prince William County

2 Days in Prince William County

Prince William County, Virginia – DC’s Countryside

Step back in time and be immersed in America’s history in Prince William County, VA. Located just 30 miles west of Washington, D.C., Prince William County is an affordable destination filled with everything from Civil War battlefields, museums and historic sites performing arts venues and exquisite shopping at both outlet stores and boutiques. Spanning from the Bull Run Mountains to the stunning shores of the Potomac River, Prince William County also offer countless outdoor recreation opportunities. www.visitpwc.com

Lodging: Check in at Country Inn & Suites -Woodbridge/Potomac Mills

Day 1 – Prince William County


Tour at Leesylvania State Park

Tour at Lake Ridge Marina

Lunch in Historic Occoquan (with Mayor Porta)


Tour & Tasting at Effingham Winery

Dinner at Tim’s Rivershore

Day 2 – Prince William County

Kayaking with Penguin Paddling at Hampton’s Landing Marina.

Early lunch at the Lazy Pig BBQ before boarding the train for home.

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