As great as the summers are, we have to admit that autumn on the Chesapeake takes the (Smith Island) cake. And while this is the best time to take the boat out cruising, it’s also a fantastic time to explore our own backyards by visiting festivals. Whether you’re into music or food trucks, beer gardens or Colonial demonstrations, there’s something for absolutely everyone here.
We’ve collected an extensive list to get you out of the house on the weekends, but this is in no way complete. Send your events to [email protected] to be included.
Family Fun
Sept. 6-8
Lures Bar & Grill Fall Fair Fest, Crownsville, Md.
Carnival treats, fall beers, and lots of shenanigans for the kids to get into, near the site of the Anne Arundel County Fair, which runs the following weekend.
Sept. 8
South Norfolk Ruritan Club’s Annual Crabfest, Chesapeake, Va.
It’s not just a shell of a good time. Beyond crabs, the Ruritan Club brings fried fish, pork BBQ, hushpuppies, and all the sides you could ask for.
Sept. 14
Family Fest on the Potomac, Piney Point Lighthouse
This is absolutely fun for everyone: from story hour to axe throwing, laser tag to vintage boats, there’s no better way to spend a beautiful Saturday in Southern Maryland.
Sept. 14-15
Mount Vernon Colonial Market and Fair, Mount Vernon
Most head to Mount Vernon for the history lessons, but during the Colonial Market you can check out artisans who work in mediums that have been somewhat overlooked by the fast pace of history. There is great shopping here, in addition to yummy food and (of course) the history.
Sept. 14-15
Maryland Seafood Festival, Sandy Point State Park, Annapolis
This festival might rival Blue Angels Day in its popularity in Annapolis. You wouldn’t believe all the ways they can use crabmeat (our favorite is the grilled cheese sandwich) but it’s also a great place to learn about the watermen and women working on the Bay today.
Sept. 21
Susquehanna Wine and Seafood Festival, Havre de Grace
Food trucks, cooking demonstrations, great drinks, and a Family Fun Zone for the kids make this weekend one of the Northern Bay’s tastiest.
Sept. 27-29
50th Annual Neptune Festival and Boardwalk Weekend, Virginia Beach
This is more than a trip for boardwalk fries. The list of events happening this weekend is a bit staggering: from a regatta to a craft fair; a surfing classic to two stages of live music; the Neptune Festival brings in over 400 vendors to create an amazing weekend in Virginia Beach.
Sept. 28
Crisfield Heritage Festival, Crisfield
Demonstrations and exhibits on watermen culture throughout the years, as well as some of the best seafood on the Bay. The Chesapeake Challenge Decoy Contest will be held simultaneously.
Oct. 4-6
Fells Point Fun Festival, Baltimore
While we have a soft spot for the Fells Point neighborhood in Baltimore, we know it’s the most fun when a festival is happening. Bring the family for live music and unique shopping, then grab a crabcake and a cold beer on the cobblestone wharf streets.
October 5
34th Annual Virginia Children’s Festival, Norfolk
Parents around the watershed dream of events like this one. There are over 100 interactive workshops, demonstrations, and activities to keep your kids entertained. The festival itself is designed for kids 10 years old and younger, so bring the littles and get ready for an epic nap time afterwards.
Oct. 19
Taste of Middlesex Festival, Deltaville, Va.
Hosted at the Deltaville Maritime Museum, there are tons of exhibits and activities for the whole family. With a car show, creek cruises, food vendors, and much more, this is a fun day for every generation in your household.
Perfect for Adults
Sept. 6-7
Wine on the Beach, Ocean City, Md.
And it’s not just wine! Celebrate area vintners as well as microbrews and craft beers. You don’t have to be a wine snob, but an enthusiasm for vino will help.
Sept. 13-14
27th Annual Virginia Wine Festival, Virginia Beach
Virginia is beginning to show up on maps as a distinctive wine region, and this festival is a great opportunity to taste wines from the various areas while meeting the men and women who are growing the grapes.
Sept. 14
Coastal Virginia Cigar Festival, Norfolk
While this festival certainly isn’t for everyone, for those who enjoy a cigar, this festival is everything. Makers Craft Brewery supplies the food and beverages, as well.
Sept. 14
Maryland Wine Festival, Westminster, Md.
Held on the grounds of the Carroll County Farm Museum, this festival offers opportunities to sample delicious wines, shop from talented artists, and enjoy live music (dancing is even encouraged).
Sept. 21
Rappahannock Riverfest, Fredericksburg, Va.
What better way to support Rappahannock River conservation than a crab feast? Riverfest is an annual fundraiser that seeks to celebrate all things attached to the beautiful Rappahannock. Please note: kids will need their own ticket if they are attending.
Sept. 22
Annapolis Oktoberfest, West Annapolis
The West Annapolis neighborhood takes a few things seriously, and Oktoberfest is one of those things. Streets will be closed off to allow food vendors and artists to showcase their wares, and you can dust off your lederhosen and enjoy some tasty brews on a cool day.
Sept. 28
Oktoberfest in the Bier Garden, Portsmouth, Va.
Sure, Oktoberfest means beer, traditional German food and music, but the under 21 crowd will have fun, too, with a magic show, glitter tattoos and balloons.
Oct. 5
DC Oktoberfest at The Wharf, Washington, DC
While this is definitely one of the best parties the Wharf puts on, we have to say the addition of racing dachshunds was the most brilliant idea anyone has ever had. Eat some bratwurst, drink some bier, and hope no one gets a video of you during the polka dancing lesson.
Oct. 5
Yorktown Wine Festival, Yorktown
A few things make this a special festival. First, Yorktown opens up its samplings to include sister cities in Germany and France. There will be Rieslings, Gewürztraminers, and Champagnes all on offer. But more than that, the incomparable Taste of Love with Bart and Jan will be performing. This duo never disappoints.
Oct. 12
Chesapeake Wine Festival, Chesapeake City
All proceeds from this great festival benefit the Rotary Club of the Chesapeake, so you can feel good attending the seminars and tastings. There are food trucks and live musicians as well.
Oct. 19
DC Wine Fest, Union Market, Washington, DC
DC Wine Fest has paired with Schneiders, a DC-area wine importer, so that all attendees to this festival will receive steep discounts for anything they want to take home with them.
Oct. 19-20
Town Point Virginia Wine Festival, Norfolk Waterfront
Town Point Park is now one of our favorite outdoor venues, and this festival is a great opportunity to hang out downtown enjoying some great weather and yummy wines before walking into town for some dinner.
Oct. 27
Yorktoberfest Craft Beer Festival, Yorktown, Va.
They had us at “unlimited tastings of beer and cider,” but the real draw of this festival is the emphasis on shopping vendors in the home improvement businesses. It’s a little liquid courage to finally commit to that three-season room deck expansion.
Music and Arts
Sept. 12-14
Annapolis Songwriters Festival, Annapolis
Annapolis is taking itself seriously as a music venue these days. This festival began small, featuring mainly local acts, but now is bringing in household name singer/songwriters such as Citizen Cope and Marc Cohn. Performances will happen around town, from coffee shops to City Dock.
Sept. 13-15
SuperNova Ska Festival, Hampton, Va.
The SuperNova brings in almost 40 of the country’s biggest ska and reggae bands to pack the grounds of Fort Monroe. We’ll all be dancing like crazy, because that’s punk.
Sept. 21-22
Annapolis Baygrass Music Festival, Sandy Point State Park, Annapolis
Headlined by one of the biggest bluegrass bands in the country, the Infamous Stringdusters, this fundraiser-in-disguise is one of the best all-ages music festivals in the area. And since it’s located on the edge of the Chesapeake Bay, you can enjoy the feeling of sand between your toes while you’re dancing.
Sept. 27-29
Chesapeake Film Festival, Chestertown
The theme of this year’s festival, Fragile Rivers/Fertile Land, pays homage to the abundant waterways and farmland that grace the Mid-Atlantic region. The short films will be followed by discussions with their creators.
Nature Festivals and Events
Sept. 8
Norfolk Botanical Gardens Mushroom Festival, Norfolk
Not those kinds of mushrooms! This festival is family appropriate, with food vendors, hands-on activities for kids, and lots of educational opportunities. Bring your foraging friends and have some fun.
Sept. 7-8
Northern Neck Native Plant Sale, Kilmarnock, Va.
Incorporating native plants into your garden is both a beautiful idea and a smart one. Attending native plant sales in your area allows you to learn what you can do to create a better living environment for both your family and the rest of the world.
Sept. 14
Tawes Garden Native Plant Fest, Annapolis
Tawes Garden is hidden behind the Maryland Department of Natural Resources building in Maryland’s capital, and having the opportunity to walk around this secret oasis is enough of a reason to celebrate. The Native Plant Fest brings in gardeners and plant experts who will give you their attention and advice for creating the backyard of your dreams.
Sept. 21
Powhatan State Park Paw Paw Festival
The paw paw fruit is certainly having a moment. This fun family festival showcases the banana-mango superfood in all its glory, but also gives you plenty of ideas of how to prepare it. There’s also live music and non-paw paw things to eat.
Sept. 21
Cape Conservation Corps Native Plant Sale, Annapolis
The Cape Conservation Corps hosts native plant sales seasonally, and it’s always a good idea to get there early. A big hangout for master gardeners, bring pictures of your garden and solicit advice from people who really know what they’re doing.
