Wine Festival in Frederick
Wine Festival in Frederick

Wine Festivals

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Wine Festival in Frederick
Wine Festival in Frederick

The arrival of fall in Maryland means amber-hued autumn leaves, cooler temps, and a fantastic selection of wine and craft beverage festivals. From the beach to the mountains traveling the scenic route along one of Maryland's amazing wine trails, you can sample a diverse selection of beverages handpicked from local, national, and international wineries, breweries, and distilleries. Maryland’s beer festivals are another ideal way to spend a crisp fall weekend, enjoying new favorites while listening to live music, perusing unique art and crafts, and enjoying delicious food from food trucks and local chefs.

1
Trinity Fest Wine, Jerk & Reggae Festival (Formerly Trio Fest)
Poolesville, August
Trinity Fest Wine, Jerk & Reggae Festival (Formerly Trio Fest)

TRINITY FEST is open for all ages and individuals looking for fun-filled moments with local and regional food, wine, and music within the DMV community.

2
Eastern's Bayside Wine and Blues Festival
Essex, August
Eastern's Bayside Wine and Blues Festival

Eastern's Bayside Blues & Wine Festival has become an annual event that hundreds look forward to attending each year.

3
Arts, Wine, Jazz & Soul Festival Fundraiser
Havre de Grace, August
Arts, Wine, Jazz & Soul Festival Fundraiser
hdgcoloredschool.net

Bring your lawn chairs and enjoy local art vendors, spectacular jazz and soul artists, phenomenal food, wines, and spirits, and a majestic view of the Susquehanna River unsurpassed in beauty. All the proceeds benefit the restoration and preservation of the Havre de Grace Colored Museum and Cultural Center.

4
SUMMER Wine Food and R&B Festival
Crownsville, August
SUMMER Wine Food and R&B Festival
eventbrite.com

Join us for the SUMMER Wine, Food and R&B Festival as we welcome live bands, wines and vendors. Bring an appetite for great music, wine and food, enjoy the fresh air, and the amazing sounds of Summer. 21+ event outdoors on grass.

5
SOCA Wine Music & Food Festival
Crownsville, August
SOCA Wine Music & Food Festival
eventbrite.com

Don't Miss out on the hottest SOCA Wine event this summer with delicious Caribbean foods, wines and SOCA Music. The SOCA Wine Festival is for everyone 21+.

6
Taste of Brandywine Wine Festival
August
Taste of Brandywine Wine Festival
Hennessycreek.com

Enjoy great food, craft beer, wine tasting, and entertainment for the entire family at our annual Taste of Brandywine festival. Bring your lawn chairs and blankets. Watch live performances by Coty The Artist & 4Ever Fam Band, Walker Red Project and DJ Frank White. We can't wait to see you there!

7
Secret Garden Farewell Summer Rnb/Gogo Music, Arts, And Wine Festival
Westminster, August
Secret Garden Farewell Summer Rnb/Gogo Music, Arts, And Wine Festival
eventbrite.com

Join host April Watts for our secret garden farewell summer R&B/GOGO music, arts and wine festival. Guests receive a complimentary glass for tastings by Dejon Vineyards, Basignani Winery, Harford Winery, and Bent Wine Co. Live music featuring The Junkyard Band, The Craig Alston Syndicate, DJ FRANK SKI, and DJ JAMAL.

8
Southern Maryland Wine, Jazz, R&B and Funk Festival
Prince Frederick, August
Southern Maryland Wine, Jazz, R&B and Funk Festival
The Original Southern Maryland Wine, Jazz, R&B & Funk Festival

The Original Southern Maryland Wine, Jazz, R&B & Funk Festival returns to bring you the phenomenal music experience you've become accustomed to. With an all new music lineup, get ready for a day of fun, great food, wine and music.

9
Maryland Wine Festival
Westminster, September
Maryland Wine Festival
Maryland Wine Festival

Don't miss the 39th Maryland Wine Festival® at Carroll County Farm Museum! Here you’ll find wineries, event partners, live music, juried artisan vendors, and local eateries. If you’re looking for the fun and excitement of the Maryland Wine Festival, be sure to stroll the Main Field!

10
Kent County R&B Neo Soul Wine Music & Food Festival
Chestertown, September
Kent County R&B Neo Soul Wine Music & Food Festival
eventbrite.com

Join us for the Kent County R&B Neo Soul Wine Festival on Saturday, September 16 as we welcome live bands, wines by Soca Wine and vendors. Bring an appetite for great music, wines, and foods. Enjoy the fresh air and the amazing sounds of R&B/Neo Soul Music. This is a 21+ event.

11
The Caribbean Wine & Food Festival
Friendship, September
Caribbean Wine & Food Festival
eventbrite.com

At this festival, you'll have the opportunity to immerse yourself in the vibrant and diverse culture of Jamaica. Savor the delectable Caribbean cuisine, from savory jerk chicken to mouthwatering plantains and flavorful curries. Indulge in a selection of exquisite wines that perfectly complement the rich and diverse flavors of the Caribbean, featuring some of the most renowned wineries, including Linganore, Ricco's Wine Adventures, Society Wines, and Reggae Wines. Feel the vibes of the Caribbean as you dance and sway to the infectious rhythms of reggae, dancehall, Afro beats, and soca, curated by talented DJs.

12
Western Maryland Craft Beverage Festival
Frostburg, September
Western Maryland Craft Beverage Festival
City of Frostburg

Join us at Hoffman Park for the annual Western Maryland Craft Beverage Festival designed to showcase Maryland's breweries, wineries, distilleries, and their products. We currently have 30 of Maryland's best breweries, wineries, and distilleries joining us with more being added. They will all be ready to let you sample their best.

13
Wine on the Beach
Ocean City, September
Wine on the Beach

Wine on the Beach has celebrated some of the finest spirits found in our region. The event spotlights varieties from vineyards such as Far Eastern Shore Winery and other Maryland vineyards, but also micro brews from our local craft breweries and domestic beers. Upon entry, all visitors receive a commemorative wine glass, which they can use to sample pours from the dozens of featured producers. Regional bands play throughout the two-day spectacle, setting a lively soundtrack as people explore booths stocked with handmade gifts and fine foods. To ensure everyone gets home safely, the event has a designated driver program that includes unlimited soft drinks and a fixed number of high fives for participating attendees.

14
Wine on the Water
Baltimore, September
Wine on the water
wineonthewaterbaltimore.com

Wine On The Water will showcase seven Maryland wineries for tasting and purchasing , Live musical entertainment of all genres and the DMV’s top food trucks, artisans and vendors.

15
Wine Down
Vienna, September
Wine Down
eventbrite.com

Zeta Phi Beta Sorority, Inc., Iota Chi Zeta Chapter will host its annual "Wine Down.” This fun-for-all event will be held at Layton's Chance Vineyard including wine tastings, food, and entertainment.

16
Harford County Wine Festival
Bel Air, September
Harford County Wine Festival
harfordcountywinefestival.com

The Harford County Wine Festival brings hundreds of wines from around the world right to your palette in a fun, lively atmosphere. More than 50 talented vendors and exhibitors, amazing discounts on all featured wines, delicious food, Oktoberfest beer garden, exclusive VIP area and much more!

17
Deep Creek Lake Art & Wine Festival
September
Deep Creek Lake Art & Wine Festival
Deep Creek Lake Art & Wine Festival

The annual Deep Creek Lake Art & Wine Festival, benefiting HART for Animals and Garrett Lakes Arts Festival, features beautifully handcrafted works by local and regional artisans, more than 200 wines to taste from Maryland and national wineries, a lounge to watch college football games and purchase beer on tap, a cigar bar, live entertainment, food, wine store, lodging packages and more, all set in the beautiful mountains of Western Maryland.

18
Susquehanna Wine & Seafood Festival
Havre de Grace, September
Susquehanna Wine & Seafood Festival
susquehannawineandseafoodfest.com

Join us at the Annual Susquehanna Wine & Seafood Festival, a family-friendly event showcasing the best of Maryland seafood restaurants and food trucks.  This waterfront festival will be held at the Concord Point Lighthouse in downtown Havre de Grace. The festival will feature 20+ local restaurants and food trucks including Jimmy’s Famous Seafood, Conrad’s Crabs, Faidley’s Seafood, and more!

19
Baltimore Wine Fest
September
Baltimore Wine Fest
baltimorewinefest.com

Experience 160+ wines from around the world, gourmet eats provided by local eateries, live music, chef cooking demonstrations, wine seminars, craft beer & spirits, unique shopping and a family zone at the annual Baltimore Wine Fest.

20
Autumn Reggae Festival at Linganore Winecellars
Mt. Airy, October
Autumn Reggae Festival at Linganore Winecellars
Linganore Winecellars

Join us for our annual Autumn Reggae Wine Festival, featuring music, food, and arts from across the region along with your favorite Linganore wines. With two full days of live entertainment, this festival is sure to be an experience you’ll never forget!

21
Howard County Hops and Harvest Festival
Columbia, October
Howard County Hops and Harvest Festival
Hops & Harvest Festival

Mark your calendars for the highly anticipated Hops & Harvest Festival, returning to the picturesque Merriweather Park at Symphony Woods. Prepare for an unrivaled experience as Hops & Harvest presents an impressive lineup of 100+ local beers, wines, and spirits, offering unlimited tastings to satisfy even the most discerning palates. Indulge in the vibrant ambiance with live entertainment, peruse artisan vendors, savor delectable offerings from fresh local eateries, engage in thrilling games, and so much more!

22
Savor Bowie Fall Food, Wine & Music Festival
October
Savor Bowie Fall Food, Wine & Music Festival
Concert for Causes

Join us for two days of complimentary wine tastings! Great food and wine vendors, exhibitors, artisans and more.  Many stages of music and entertainment for the entire family!

23
Whiskey, Wine & Fire
Timonium, October
Whiskey, Wine & Fire
baltimore.whiskeywinefire.com

This exclusive foodie celebration will feature whiskey bars, elegant wines & cocktails, great music, food stations, food trucks and intimate fire pits throughout. Relax around the fire gardens and enjoy an inspired take on fire-kissed BBQ, open fire cooking, specialty grilling, and drink pairings. Enjoy the firebreathers and artists set the night ablaze. Please dress appropriately, the event is outdoors.

24
Wine at the Shrine
Ellicott City, October
Wine at the Shrine
wineattheshrine.org

We hope you join us for a day of delicious beer and wine, local food trucks, live music, hayrides, Little Portion Farm tours, and kids activities – all on the beautiful grounds of the Shrine of St. Anthony.

25
Fall Back Ciders, Spirits, And Wine Fest
Boonsboro, November
Fall Back Ciders, Spirits, And Wine Fest
Interstate Festival Group

The Fall Back Ciders, Spirits & Wine Fest takes place at the Washington County Agricultural Education Center just south of Hagerstown. This annual event will see over 125 varieties of libations represented by over 25 combined wineries, cideries, distilleries and breweries. All alcohol samples are included in your admission in your festival tasting glass. Take part in numerous games and contests, browse and shop from dozens of vendors, and chow down on some scrumptious grub from the best local food vendors. Don't forget to bring your dancing shoes and jam with The Reagan Years!