9/16: Maryland Wine Festival
This outdoor festival at the 143-acre Carroll County Farm Museum will have local wine vendors, live music, and shopping with items from juried artisans. You can also browse produce from local eateries and bottles of wine from the retail shop. 500 South Center St, Westminster. 11 a.m.-5 p.m. $30

9/23: Trifecta Food Truck and Music Festival
At the Timonium Fairgrounds, the Trifecta Food Truck and Music Festival is returning with 35 food trucks, live music from 12 bands, and more than 50 vendors. There will be several bars serving beer and cocktails, as well as activities like axe throwing, a mechanical bull, and a photo op with the Oriole bird. 2200 York Road, Timonium. 11 a.m.-10 p.m. $25. Kids 12 and under are free.

9/23-24: The Big Dill World’s Largest Pickle Party
Power Plant Live is bringing back its ode everyone’s favorite brined snack. The event will feature samples and jars for sale by artisan pickle companies. There will also be live music performances, The Big Dill World Pickle Eating Championship, a brine chug challenge, pickle-themed cocktails, and food and carnival games. 34 Market Pl. 11 a.m.-7 p.m. Five tiered ticket passes available for purchase

9/28: The World is Your Oyster Festival
If you love seafood and oysters, then Oyster Recovery Partnership’s WIYO Festival is for you. The B&O Railroad Museum will host local oyster farms for visitors to mingle with. At each table, farmers will be teaching how to shuck, as well as passing on oyster recipes. Beer, wine, and cocktails will be available, in addition to live music and a raffle. 901 W Pratt St. 5-9:30 p.m. $125 

9/29-10/1: The Maryland Italian Festival
The Harford County Equestrian Center will be holding what’s billed as Maryland’s largest Italian festival. Vendors (look out for familiar favorites such as Di Pasquale’s, Liberatore’s, and Pappas Seafood Co.) will be serving Italian food along with wine, beer, and liquor. Attendees can partake in wine and cooking demonstrations, live entertainment, carnival rides, and a bocce tournament. 608 N Tollgate Road, Bel Air. Sept. 29, 5-11 p.m., Sept. 30, 11 a.m.-11 p.m., Oct. 1, 11 a.m.-7 p.m. General admission is $10 and kids 12 and under can go for free.  

9/30: Maryland Microbrewery Festival
The 17th Maryland Microbrewery Festival will be held on Sept. 30 at Union Mills Homestead Park in Westminster. There will be a wide selection of Maryland breweries slinging samples, plus food vendors, live music, craft vendors, and seminars to teach attendees about homebrewing. 3311 Littlestown Pike, Westminster. 11 a.m.-6 p.m. $25 for a ticket bought in advance for adults who wish to sample drinks. Kids 12 and under are free. 

9/30: Pigtown Festival
On Sept. 30, this beloved Southwest Baltimore neighborhood tradition is returning in its 21st year. Aside from the time-honored pig race, “Squeakness,” look out for more than 80 vendors with local food, craft beer, live music, and arts and crafts, as well as a free kids zone. Sales will benefit Pigtown Main Street to revitalize the Washington Boulevard commercial corridor. 763 Washington Blvd. 12-7 p.m. Free. 

10/6-8: Fells Point Fun Festival
Returning the weekend of Oct. 6-8 on the waterfront in Fells Point, this fall tradition boasts hundreds of food and drink vendors (fan-favorites often include steamed buns from Ekiben and crab tots from Alexander’s Tavern) along with live music and shopping from artisans. All drink ticket sales benefit the Society for the Preservation of Federal Hill and Fells Point. Waterfront in historic Fell’s Point. The festival runs along Thames Street from Caroline to Wolfe and is bordered by Aliceanna on the north edge. Free. 

10/7: Hops & Harvest Festival
On Oct. 7, the Hops & Harvest Festival will be taking place in Symphony Woods in Columbia, where guests can experience wine, beer, spirits and cider tastings from local breweries from 12-5 p.m. A selection of vendors will also be selling food to pair with live music and fun activities. 10431 Little Patuxent Parkway, Columbia. 12-5 p.m. General admission bought in advance is $45

10/7-8: Baltimore Taco Festival 
The sixth-annual Baltimore Taco Festival is being held at Power Plant Live on Oct. 7 and 8. Taco lovers can expect more than 25 taco and food vendors, as well as bars and beverage stations selling margaritas, beer, tequila flights and more. 34 Market Pl. 2-8 p.m. $10 

10/7-8: Autumn Reggae Wine and Music Festival
Road trip to Linganore Winecellars in Mt. Airy on Oct. 7 and 8 for this reggae-themed festival full of music, wine, food, and local art. 13601 Glissans Mill Road, Mt. Air. 10 a.m.-6 p.m. General admission starts at $37 

10/13-14: Maryland State BBQ Bash
This barbecue street festival is the home of the Maryland State Barbecue Championship, which pits more than 50 teams against one another to see who makes the best smoked snacks. The winner moves on to the Jack Daniel’s World Championship Invitational in Tennessee. 2 S Bond St, Bel Air. Oct. 13, 4-10 p.m. and Oct. 14, 12-10 p.m. Free

10/14: Oyster Stroll
To raise awareness of the importance of oyster aquaculture in the Chesapeake Bay, downtown Westminster will host this event for guests to slurp oysters, groove to live tunes by Amish Outlaws, and sample sips of wine and beer. 45 West Main St, Westminster .12-4 p.m. $15  

10/14: Whiskey, Wine and Fire
This outdoor nighttime festival will include whiskey bars, wine and cocktails, food stations, music, food trucks, and fireplaces throughout the Maryland State Fairgrounds on Oct. 14. Guests will be able to enjoy food and drink while also shopping at local craft exhibitions. 2200 York Road, Timonium. 5-9 p.m. $69

10/21-22: OktoBEARfest
The Maryland Zoo will be holding its German-themed festival with unlimited samples of beer, wine, seltzer, and cider. The two-day event also includes live music, local vendors, and all-day admission to the zoo. 1 Safari Pl. 1-6 p.m. $65.

10/22: Baltimore Pit Beef Festival
West Covington Park is hosting the Baltimore Pit Beef Festival on Oct. 22, which will have a surplus of the Old Line State’s signature smoked meat. There will also be oysters, more than 50 beers, a selection of Crushes, snowballs, and live music. 101 W Cromwell St. 1-5 p.m. $42 

10/28: Das Best Oktoberfest
On Oct. 28, more than 120 local beer and wine vendors will be at the Maryland State Fairgrounds for this local Oktoberfest celebration. The German festival will offer traditional eats, music, dancing, and costume contests. 2200 York Road, Timonium. 1-5 p.m. $40 

11/4: Sykesville Craft Beer Festival
Downtown Sykesville is highlighting more than 50 sudsy brews at this annual event. There will also be food trucks, artisans, and live music. Main Street, Sykesville. 12-4 p.m. $50

11/4: Baltimore Craft Beer Festival
Grab your crew and head to Canton Waterfront Park for the Brewers Association of Maryland’s celebration of our state’s robust craft beer scene, where breweries from all over will offer samples of their ales, lagers, ciders, and meads. The festival will also have live music, shopping, and food trucks. 3001 Boston St. 12-5 p.m. Tasting pass, $45, Beer Geek pass, $65 

11/26: BRRR Festival
On Nov. 26, the Maryland Zoo will be unveiling its annual holiday lights with unlimited beer and wine sampling. Along with the light show, there will be carnival rides for little ones. 1 Safari Pl.  5-8 p.m. Adults 21 and over, a ticket costs $61. A non-sampling ticket is $36.

Source