Fun and Exciting Events Worth the Drive from Washington DC

Crisp cool weather, apple picking, and pumpkin spiced anything (and everything) has hit the East Coast. Autumn is here and there are tons of celebratory festivals, art and music shows happening in and around Washington, DC.

Some of our favorite Washington DC events take place a drive away in towns and cities across the Mid-Atlantic states. From Philadelphia and Baltimore to smaller towns like Easton, PA and Winchester, VA there is more than just pumpkin juice brewing this season.

When DC is your main hub, hop in the car and explore these great autumn events across the region.

PA Bacon Fest
PA Bacon Fest

Photos Courtesy of Discover Lehigh Valley

PA Bacon Fest

Who can resist a bacon festival? Not us! Located in Easton, PA, the PA Bacon Fest takes place in early November. Visitors can enjoy bacon-themed culinary treats, cheer on their favorite pig or pooch in the annual Pig and Wiener Dog Races, and sample beers from the Weyerbacher Brewing Company.

Where: Lehigh Valley, PA
When: early November

Philadelphia Mural Arts Month
Philadelphia Mural Arts Month

Photos courtesy of Steve Weinik/

Philadelphia’s Mural Art Month 

Did you know that Philadelphia is the unofficial mural capital of the U.S.? It’s true! And I’m not just saying that because I grew up in Philly. The Mural Arts Project started back in the 1980s to combat the rampant graffiti throughout inner-city Philadelphia. By hiring graffiti artists, the city was able to bring local pride into some of the poorest neighborhoods. Philadelphia has so many murals that they are now in their second and third reinvention of the mural, while other cities are just starting to find their artistic voice.

Mural Art Month focuses on empowering a sense of community and civic voice through art across the city. Watch artist while they create murals, sit in on panel discussions, participate in workshops and watch as new mural projects are dedicated across the city. Each has a powerful message, and ties back to the city and the community it is placed into in some way. If you are new to the Philly mural scene, make sure you hop on an Art Walk to get a real taste for the mural history of this city.

Where: Philadelphia, PA
When: October

Baltimore Fleet Week
Baltimore Fleet Week

Photos courtesy of Maryland Fleet Week & Air Show Baltimore

Maryland Fleet Week and Air Show Baltimore

Head north to Baltimore for the Maryland Fleet Week and Air Show Baltimore taking place in early October. Tour more than a dozen ships from the U.S. Navy and Coast Guard, Canadian and British Navy ships. The USAF Thunderbirds and demonstrations from the F-16 Fighting Falcon will be taking place over the weekend, and is definitely something young (and old) aviation enthusiasts won’t want to miss. In addition to the ships and planes, there are a number of different festivals scheduled throughout Fleet Week.

Two tips: Friday is when the Thunderbirds do their practice runs. The crowds are a lot smaller than the weekend too. Many of the ships are also open to tour. Go on Friday afternoon if you have time and the kids have a half day. Oh and moms, you can take a selfie with a sailor at happy hour on Friday. Check the schedule for exact times and locations for that one.

Where: Baltimore, MD (Inner Harbor, Fells Point, Canton and Locust Point, Rash Field, Maryland Science Center and the National Aquarium. 
When: early October

Annual U.S. Oyster Festival

Maryland doesn’t just love her OLD BAY® Seasoning and crabs, she loves her oysters too. Get ready to experience the National Shucking Championship with competitors from across the United States. The winner gets to compete in Galway, Ireland for the World Shucking Championship. Yes, that is a real thing. 

For those not participating in the contest, have no fear, there is plenty for you to do. There is live music, local foods, arts, crafts, craft beer tasting, and loads of family fun.

Oh, and did we mention that there is also the National Oyster Cook-Off happening? Do not miss your chance to get inspired to create your own amazing oyster dishes and maybe even enter next year. 

Where: St. Mary’s County Fairgrounds in Leonardtown, MD
When:  late October

Renaissance Festival-Maryland 
Maryland Renaissance Festival

Photos Courtesy of Maryland Renaissance Festival

Renaissance Festival-Maryland 

Maryland is home to the second largest Renaissance Festival in the country. Enter Revel Grove, a 16th-century English village, where King Henry VIII and his court preside over the festivities. Roam around the 24-acre site featuring more than 250 performers on ten different stages. The festival is home to 130 craft shops, 42 food and beverage emporiums and a host of games and attractions.

LARPing (Live Action Role Playing/wearing period costumes) is highly encouraged. More than one fairy, goblin and damsel in distress who does not work the festival will be in attendance. I guarantee it. In fact, if you see two beer wenches, say hi to my friend and her mom who were there last weekend.

Where: 1821 Crownsville Road, Annapolis, MD 
When:  Saturdays and Sundays, August through late October

Not sure what a Rennaissance Faires are all about?
Neither was I until I went.
CLICK to find out more!

Jackson Ward Richmond

Photo courtesy of Richard T Nowitz/Visit Richmond

Richmond, VA 2nd Street Festival

The 2nd Street Festival, which takes place in Jackson Ward, an area once known as “the Harlem of the South,” celebrates the rich culture of the neighborhood. The historically African-American community is features four stages of live musical entertainment, food vendors, a marketplace and Artists Row to Shop, and welcomes locals and out of towners to experience why this neighborhood is the place to be in Richmond.

Where: Jackson Ward, Richmond, VA 
When: early October

Fire Flour and Fork

Photo courtesy of Visit Richmond

Fire, Flour, and Fork

A four-day culinary experience- do you really need more convincing to drive south?

Fire, Flour, and Fork is a series of events taking place around downtown Richmond. Previous years have explored themes like Your Fork, Your Future “exploring the power of the recipe box and the stories recipes tell with families and social/political movements.” Sign up for dinners, tours, demonstrations and booking signings. Do it quickly and stalk the website. Tickets can be purchased online and they sell out fast.

Where: Richmond, VA  
When:  early November

Richmond Folk Festival

Photo Courtesy via Visit Richmond

Richmond Folk Festival

The Annual Richmond Folk Festival takes place on Brown’s Island (although the location can change from year to year) with performing groups on seven different stages and all the dancing, crafts, food, and beer you could want. Themes change every year, but the 2018 favorite was “Masquerade.” Visitors could explore costuming traditions from across the globe, including Buddhist ceremonial masks and Carnival costumes.

Where: Downtown Richmond, VA waterfront 
When:  mid-October

Autumn Events Worth the Drive from Washington DC

Photo courtesy of Visit Winchester VA

Oktober Fest

Did someone say beer?! The Annual Oktoberfest happens throughout Old Town Winchester in mid-October. Entertainment is free to everyone, kids included, and beer and wine tastings can be purchased via advance or day-of tickets (tickets get you six tastings and a souvenir beer stein).

Local and imported beer and wine are served, as well as several German edibles you and your kids will love. Past bands and entertainment have included Alt Washingtonian Schuhplattler Verein the “Original Bavarian Dance Club of Washington DC with over 30 dancers dressed in authentic German costume.

Please note: Lederhosen wearing is encouraged.

Where: Old Town Winchester, VA. Loudoun Street Walking Mall, Taylor Pavilion, and the Courthouse Lawn.  
When:  mid-October

Autumn Events Worth the Drive from Washington DC

Photo courtesy of Visit Winchester VA

Winchester Frontier Days and Rodeo

The Winchester Frontier Days began as a tribute to Buffalo Bill and the 100th anniversary of his visit to Winchester in 1916. What better way to celebrate than with shootouts, roping demonstrations, artisans, crafters, and a nice lunch? Admissions are $5 a person, $20 a family, and children three and under are free. Not too bad for a weekend excursion.

Where: 2502 N. Frederick Pike, Winchester, VA 
When:  early October

Williamsburg Art and Music Festival
Williamsburg Art and Music Festival

Photo courtesy of Williamsburg, VA

Art and Music Festival, Williamsburg, VA

Taking place in Merchant Square, in the heart of Colonial Williamsburg, the Art and Music festival is free and open to all. Artists from all over the country gather in Williamsburg, VA to showcase their work while consumers enjoy the local food vendors, watch live performances, and do a little early holiday shopping.

Where: Williamsburg, VA 
When:  early October

Mariner's Arrrtober Festival

Photo courtesy of Mariner’s Arrrtober Festival

Mariner’s Arrrtober Festival

Enjoy a full day of family fun with pirate-themed activities including pumpkin painting, hayrides, pirate storytelling, and more. Snack on food from local food trucks and craft beer while you listen to live music.

Where: Mariner’s Museum and Park, Williamsburg, VA 
When:  mid-October

AutumnFest, Shenandoah County

Photo courtesy of Shenandoah County

AutumnFest, Shenandoah County

AutumnFest features over 30 craft beers, wines and spirits, and a BBQ tasting. Entertainment includes harness racing, log splitting, and shopping various craft vendors. Dates, ticket information and pricing is available online.

Where: Woodstock, VA 
When: mid-October  

National Apple Harvest Festival
National Apple Harvest Festival

Photos courtesy of Destination Gettysburg

National Apple Harvest Festival, Gettysburg, PA

For more than 50 years, families have been flocking to the annual National Apple Harvest Festival to enjoy delicious food, live music and tons of craft vendors. We love it because we can load up on our favorite hard cider made right in Gettysburg, PA. You can also check out antique cars, steam engine displays, orchard tours, a petting zoo, and an appearance by the Pennsylvania Apple Queen! Tickets are available online or at the door. Just don’t forget to take home a bushel of apples. Your kids will never forgive you if you don’t.

Where: South Mountain Fairgrounds, Gettysburg, PA 
When:  early October

Adams County Pour Tour
Adams County Pour Tour

Photos courtesy of Destination Gettysburg

Adams County Pour Tour

Did you know that Gettysburg, PA (in Adams County) is the fifth largest apple producer in the country? They also make wine and brew beer too.

You can now go on your very own Pour Tour with the Adams County Pour Tour passport booklet that helps you visit all of the wineries, breweries, cideries and even a distillery or two across the county. What better excuse to get out and explore one of Central PA’s most popular historical destinations, even if you don’t feel like sitting on a cannon.

Where: Adams County, Gettysburg, PA 
When: ongoing

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Washington, D.C. Travel Resources

Your Washington, D.C. vacation doesn’t have to be stressful. We’ve got the resources you need to plan your trip and make the most out of your time in the city and surrounding area. If this is your first time to the capital region, check out our Washington, D.C. trip planner and itineraries.

For transportation, check out our D.C. driving guide and our guide on how to ride the metro. For those flying in, you’ll want to read our guides to BWI, DCA and IAD airports.

Dive into our things to do in D.C., which is always being updated and evolving to make sure you have the latest and greatest activities to fill your checklist of things to do. Don’t forget about food, the real reason we all travel, right? Our Washington, D.C. restaurant guide will get you started and lead you into neighborhoods full of delicious treats.

For more resources, check out our pages on Baltimore, Richmond and beyond.

Where to Stay in Washington, D.C.

Budget: When it comes to Washington, D.C. budget hotels, prices vary depending on the season. In the middle of October, a four-star hotel could be under $150, while in December it may be over $400. At any given time of year, though, Hotel Hive is a safe bet for value when it comes to resting your head. If you are looking for a hostel, Hi Washington D.C. Downtown is well located for exploring all of the D.C. museums, restaurants and bars at the fraction of the price of a hotel. Check rates and availability here.

Mid-range: Every USA hotel chain can be found in Washington, D.C., but stay at the St. Gregory Hotel when you want a local touch. The modern, light-filled rooms will welcome you to the city, whether you are in a studio or suite with wraparound terrace. The hotel is walking distance to Georgetown, the National Mall and Embassy Row, making it easy to explore without a rental car. Check rates and availability here.

Luxury: You are spoiled for choice when it comes to luxury hotels in Washington, D.C. We love cozying up at the Graham Georgetown, a sweet little boutique hotel in one of the hottest neighborhoods in the city. Check rates and availability here. Major hotel brands like The Fairmont, Mandarin Oriental, Ritz-Carlton, Four Seasons Hotel Washington D.C. and St. Regis Washington D.C. all have outposts here as well. If you want something a bit more historic, we recommend The Jefferson, Washington D.C. Ninety-nine rooms in this luxury boutique hotel bring together an attentive staff, petite spa, and the Michelin-starred Plume restaurant with all of the history you could hope for when you are in the nation’s capital. Check rates and availability here.

Family-friendly: We always gravitate towards the Kimpton hotels whenever we are traveling with kids. Kimpton Hotel Monaco Washington D.C., once the General Post Office building, is located in the Penn Quarter neighborhood just four blocks off the National Mall near the National Gallery of Art. Price point is mid-range, depending on the time of year you visit. Parents will love the nightly wine events and evening nightcap perks as well as complimentary coffee and a tea bar each morning. Kids will love that they can borrow a fish friend for their stay, and that there is always a treat on hand that they can enjoy, and the robes are just their size. Kimpton also has adult and child-size bikes to borrow so you can cruise around town during your stay. Check rates and availability here.

Planning a Trip to Washington, D.C.? Don’t Forget Travel Insurance!

Whether you are traveling domestically or coming from an international destination, travel insurance is a must for anyone coming to Washington, D.C. You will be exploring both inside and outdoors; hiking may even happen if you get adventurous. You could find yourself on a Segway or bike tour. The city is highly populated and accidents and crime do happen. This is not to scare you, but to prepare you for what could occur when you are checking out the free museums, exploring neighborhoods, finding the best food and learning about the local street art. Should something happen, travel insurance has you covered. Check rates and availability here.

We recommend and use Allianz Travel insurance. Our family is covered under a household plan, but their individual plans are just as robust if you are a solo traveler or a couple looking to get away. I’ve been a customer for more than five years and have always been in good hands with the Allianz team.

Get your travel insurance quote for your DC trip here.

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