Fun Times at Wine Festivals: Wine in the Woods

It’s more than wine. Wine in the Woods is all about the crowds, the music, the colors, the socializing… and yes, the wine, which is the excuse for some 30 thousand people to gather in one spot to listen to some good music (and some not) and to enjoy the outdoors and of course, to drink some wine.

Featuring more than 30 wineries, Wine in the Woods is Maryland’s largest and the region’s second largest wine festival, and it happens every year on the weekend after Mother’s Day. This festival began in the early 1990s; each year the festival has grown larger, and now attendance is expected to be 30 thousand or greater. It is also fairly typical of wine festivals, bringing together local wineries, food vendors, live music, and local artisans. The festivals and events bring the region’s finest wines to you in one location, and is a great way to decide in advance if a winery is worth visiting.

I go almost every year. This year I volunteered for a winery I’m a big fan of — Red Heifer Winery. I really like this winery — I like their energy as well as their wines, and owners Yvonne and Kevin are just nice people that you hope will succeed. So this time I was on the other side of the wine pourer table, living out my fantasy of working at a winery. I will not be quitting my day job anytime soon.

It was a lot of fun, although some folks stepping up to the sample bar are there just to get drunk, and that’s not amusing or fun to be around. I feel for the wineries — a lot of them do most of their sales via these wine festivals and at their wineries, and they don’t want to alienate any potential customers, but some of the potential customers can be rude. It was clear some folks were just there to drink and get drunk, one tiny wine sample at a time. But most folks are nice. Not that many actually want to hear about the wines, which is one of the things I most like about going to wineries, but in the press of the crowd, there’s really not that much time to spend with individuals. Some people expressed their insecurities: “I don’t know much about wine.” I always assured them, “You know what you like — that’s good enough.”

After our shift — most wineries will only ask their volunteers to work 2 or 3 hours — we got to walk around and sample and enjoy the rest of the day. The nice thing about volunteering is you don’t have to pay the entrance fee and you get a Wine in the Woods souvenir glass and can sample as much as you want (not while you’re volunteering, though). Some wineries will offer their volunteers free t-shirts or a free bottle of wine or at least a reduction in the cost of wine purchases. Check with your favorite winery regarding whether they want any volunteers and what they offer their volunteers. I was happy just to save on the $40 entrance fee (I turned that savings around into wine purchases).

Wine in the Woods offers a number of bands, playing at two stages. There are also a variety of juried arts and crafts booths. Interestingly, the festival also sponsors wine education seminars as well, such as Wine Tasting 101, Maryland White Wines, Red Wines, and Sweet and Dessert Wines. We attended the Red Wines seminar last year and found it very interesting — we were walked through tastings of several red wines, with a discussion of how to taste — how to move the wine through your mouth — how to sniff, and so forth. I came out of that seminar not feeling so quite as dumb as I swirled and swished and spit.

You can count on having a number of food vendors there as well. Some delicious food was being offered — from crab melts to chicken gyros to grilled sausages. Yum! But the food can be quite expensive, so save a few bucks (and spend it on the wine instead) by packing a picnic, easy to do since coolers and packages are allowed into the venue (although this is not true of all wine festivals). Be sure to purchase a bottle of wine from your favorite winery to enjoy with lunch!

As much as I enjoy this event — and I’ll probably be back next year if Red Heifer Winery will take me back as a volunteer — I have to say that, after a year of checking out Maryland’s (and now several of Pennsylvania’s) local wineries, I much prefer the quieter atmosphere of sampling wines in the wineries themselves. I appreciate the interaction with the servers, who are often the owners, and the discussion about the wines and the winery itself. However, at Wine in the Woods, I took advantage of having my favorite wineries all in one location to make a few purchases of wines I particularly enjoyed over the past year.

Tip #1: Bring fold-up chairs and blankets, even your own picnic, to spread out under the trees to listen to music. Plan to stay the whole day. Although well shaded, you can still get a sunburn — make sure you use sun block!

Tip #2: If you have a designated driver (and you should), buy a bottle of wine for him or her to enjoy at a later time. They deserve it!

Tip #3: Bring cash. Many of the food vendors only accepted cash. Most, if not all, of the wineries accepted credit cards.

Other wine festivals this year:

Great Grapes! Wine, Arts & Food Festival 
May 31- June 1

Great Grapes! is Baltimore’s premier casual wine tasting with great Maryland wines available for tasting. Take your souvenir tasting glass as you enter the festival and stroll from tent to tent and table to table tasting and sampling the rich Heritage of Maryland vines. Oregon Ridge Park 

Annapolis Arts, Crafts & Wine Festival
June 6-7
Fine, juried arts and handmade crafts and winetastings from more than 25 Maryland wineries, smooth jazz all day long, delectable cuisine, and activities for the whole family.
Navy-Marine Corps Stadium, Annapolis

Southern Maryland Sun & Music Festival June 7-8Come out and help us celebrate 2 days of great fun while supporting Southern Maryland’s Local charities, Wineries, Artists and Musicians. Activities include Maryland Wine Tasting, Craft Beers, BBQ, Arts and Crafts, a Kid’s Zone, Hot Air Balloon Rides and much more.Calvert County Fairgrounds Prince Frederick 

Taneytown Wine and Jazz Festival 
June 21
Local wine vendors, artisans, forgotten artists, food and music, children’s activities. 

Taneytown, Carroll County 

Grape Blossom Wine FestivalJune 22
Sample wines from Eastern Shore wineries.  Enjoy entertainment all day, plus tours of the winery, craft vendors, souvenir glass, and more!

Layton’s Chance Winery (4225 New Bridge Road in Vienna, MD)

Cecil County Food & Wine Festival 
July 19
Enjoy a day of Cecil County and Maryland wines, wine tastings, local foods, crafters, artists and live music.
North East Community Park, North East, Cecil County 

Uncorked Wine and Music Festival 
August 23
Enjoy the best wines from across the state, cooking demonstrations and two stages of musical entertainment at Uncorked!
36 Maryland Ave., Rockville, Montgomery County

Deep Creek Lake Art & Wine Festival 
September 5 – 7, 2014 
The festival includes wine, regional artists, children’s area, silent auction, live music and lots more!
Garrett County Fairgrounds, Deep Creek Lake, Garrett County 

Maryland Wine Festival 
September 20-21, 2014 
Take pleasure in Maryland wine with tastings from 30+ wineries, live music, foods from local restaurants, arts and crafts and wine education seminars. 
Carroll County Farm Museum, Westminister, Carroll County 

Wine on the Beach 
September 26-27, 2014 
Wineries from across the mid-Atlantic region, arts and crafts,
continuous entertainment, food, and more.

Ocean City, Worcester County 

Autumn Wine Festival 
October 18-19, 2014 
One of seven Maryland Wineries Association-sanctioned festivals. Tastings from 20 Maryland Wineries. 
Salisbury, Wicomico County

Wildcat Ridge Music & Wine Festival 

June  7
Relax and listen to live music while you sample some of Pennsylvania’s finest wines. Purchase a variety of delicious foods from vendors. Artisans will be selling their crafts, some centered around a wine festival theme.
Gratz Fairgrounds, Gratz, PA

Brandywine Valley Wine Trail Food and Wine Festival 
June 14
Taste your way through the offerings of the Brandywine Valley and enjoy live music all day! 


September 26-28
Twelve wineries, twenty bands… Part wine festival, part music festival, part arts and crafts festival — and a whole lot of fun! 

Northeast, PA

Hops, Vines & Wines Festival
July 19
Central PA’s fines beer and wine festival.
Downtown Selinsgrove, PA

Horse & Hound Wine Festival 
July 12
Come join us on the gracious grounds of Johnson’s
Orchards, located in scenic accessible Bedford, VA.

39th Annual Virginia Wine Festival
September 13-14
Showcases more than 50 Virginia wineries
Great Meadow Equestrian Center, The Plains, VA

Carytown Food & Wine Festival
October 5
On the streets of Carytown, you can try the finer things of life. The festival spotlights not only the great wines of the region, but the incredible food prepared by area restaurants. 

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Have you daytripped somewhere interesting? I’d love to hear what you’re doing! Email [email protected] if you’re interested in being a guest-blogger!