Horse racing has always been a beloved custom and cause for celebration in the Land of Pleasant Living. For the 141st year, partake in the local tradition that is Preakness, which is back and better than ever, riding off the high of last year’s American Pharaoh sweep.
Ryleigh’s Oyster Third Annual Triple Crown Series
May 7, 21, June 11: The county location of Ryleigh’s Oyster is transforming into a race party headquarters this season. With events planned for each jewel of the Triple Crown, the bar is going all out with classic cocktails, hat contests, and specialty snacks like biscuits with ham and pimento jelly, spiced peanuts, and fried green tomatoes. During the Preakness party on May 21, dress to the nines, sip Sagamore Spirit Crushes, and enjoy the sounds of country rocker Jenny Leigh during a special post-race performance. 22 W. Padonia Road, Lutherville-Timonium, 410-539-2093
Third Annual America’s Best Racing Pre-Preakness Party
May 18: Rub elbows with jockeys, sip Black-Eyed Susan cocktails, and enter to win swag like Preakness tickets and signed racing memorabilia at this pre-party to benefit the Thoroughbred Aftercare Allegiance. Mt. Washington Tavern, 5700 Newbury St., Free, 7-10 p.m., 410-367-6903
Turf Valley’s Preakness Celebration Hot Air Balloon Festival
May 19-21: Gather the family and head to Ellicott City to take in the sights and sounds of this annual fete, which offers everything from arts and crafts and food truck fare to tethered flights and grounded hot air balloon walk-throughs. Guests are also invited to watch 25 illuminated balloons light up the skyline to the beat of choreographed music during nightly glow-in-the-dark shows. Turf Valley, 2700 Turf Valley Road, Ellicott City, Free admission, 410-465-1500
BMore Around Town Pre-Preakness Party Packages
May 21: If you’re worried about parking and Uber surge-pricing on Preakness day, the tailgating experts at Bmore Around Town have got you covered. Round-trip transportation with beer on the bus and pregame brunch specials are highlights of this all-inclusive package offered at Mother’s Grille in Federal Hill and Claddagh Pub in Canton. 1113 S. Charles St. and 2918 O’Donnell St, $45
May 21: Don your best spring formal attire and trot over to Port Discovery for this horse-themed charity event that features food and drink specials and music spun by DJ Candy D. All proceeds benefit Mayor Stephanie Rawlings-Blake’s Hire One Youth initiative. Port Discovery, 35 Market Place, 8 p.m., $50-100.
Preakness Party Package at Mad River
May 21: This Federal Hill favorite is offering an all-inclusive party package for Preakness, which will include a breakfast buffet, bus transportation, one all-you-can-drink MUG Club ticket to Infieldfest, and open-bar access upon return. 1110 S. Charles St., 410-727-4333
Hats & Horses: An Evening at the Races
May 23: Bowties and big hats will be plentiful at this jockey-themed function featuring gourmet eats from the likes of Baldwin’s Station, Classic Catering, and La Scala, to benefit Meals on Wheels of Central Maryland. The Grand Lodge, 304 International Circle, Cockeysville, 5:30 p.m., 443-573-0945, $150
The Tavern Derby at Mt. Washington Tavern
In honor of horse-racing season, this neighborhood bar is rolling out a new collection of cocktails. The Preakness-inspired menu features the tavern’s takes on classic hunt club drinks such as the “Tavern Susan,” the “Tavern Belmont,” and the “Tavern Julep,” made with mint, simple syrup, Bullet rye, and club soda. All drinks are served in a commemorative, take-home glass. 5700 Newbury St., 410-367-6903
Polo Bar at Hunt Valley Inn
Despite a recent $15 million renovation, The Hunt Valley Inn’s equestrian roots have been maintained through its updated horse-country decor. Snag a seat at the hotel’s Polo Bar to sample specialty cocktails and small plates featured on a “Triple Crown” menu this season. Offerings include mint juleps, Black-Eyed Susans, and Belmont Breezes, as well as bites like ham and manchego crostini, spicy chicken skewers, and stuffed jalapeños.Other race-inspired options include Oaks Lily (Stoli vodka, triple sec, cranberry juice, and simple syrup) and Down the Stretch (Grey Goose, blue curacao, grenadine and lemon-lime soda).245 Shawan Road, Hunt Valley, 410-785-7000
Preakness-Inspired Cocktails at Colette
Bar manager Crystal Wack has added a slew of classic cocktails to the menu at this Station North newbie in honor of Preakness. Order traditional mint juleps, Black Eyed Susans, and Belmont Breezes, or try the new “Sir Barton” cocktail, which is Wack’s take on the classic Southside. 1709 N. Charles St., 443-835-2945
Sunrise at Old Hilltop
May 17-20: Enjoy a behind-the-scenes look at the Preakness contenders’ morning workout, with a tour of the barn and view of the sunrise. Pimlico Grandstand. 6-9 a.m.
Preakness Post-Position Draw
May 18: Officials will pull starting positions for the middle jewel of the Triple Crown, which also will be streamed live online. Pimlico Sports Palace. 5 p.m.
Preakness Alibi Breakfast
May 19: Join trainers, owners, and jockeys for breakfast as they tell fans and the media what it takes to make it to Preakness and possibly become a racing legend. Pimlico Race Course. 9:30 a.m.
Jockey Autograph Session
May 20: Fans will have the chance to meet their favorite riders before their big race on Saturday. Pimlico Grandstand. 10-11 a.m.
Black-Eyed Susan Day
May 20: The day before the mane (ahem) event, watch this historic filly race, enjoy an infield concert, sip Black-Eyed Susan cocktails, and attend a women’s networking lunch, all to benefit Susan G. Komen Maryland and Thoroughbred Aftercare Alliance. Pimlico Race Course. 11:30 a.m.
May 21: Don't miss the party of the year, with big-name musical acts like rapper Fetty Wap (of "Trap Queen" fame), electronic duo The Chainsmokers (remember that "#Selfie" song?), and Towson's own All Time Low. Pimlico Race Course. Doors open at 8 a.m.
141st Preakness Stakes
May 21: The big day has finally arrived: the 141st Preakness Stakes! Fourteen of the nation’s best jockeys and horses compete to win the second jewel of the Triple Crown. Pimlico Race Course. Doors open at 8 a.m. Race begins at 6:18 p.m.