October Happenings: Seasonal Sips & Spooky Celebrations

Every Thursday at Azumi Houston: Enjoy $2 Lychee, Vodka & Gin Martinis at the bar and on the patio from 3 pm – close!
Every Thursday at Monarque: Enjoy $2 Espresso Martinis from 5 pm – close throughout the restaurant. Live entertainment starts at 7:30 pm!

October 3rd: The Choptank and Ouzo Bay are proud to take part in Maritime Magic, one of Baltimore’s biggest waterfront celebrations. This lively evening brings together local flavors, live entertainment, and a vibrant crowd—all in support of Living Classrooms Foundation. Stop by our tables to enjoy signature tastes from both restaurants as we join fellow Baltimore favorites in raising a glass to a great cause.

October 4th: Loch Bar, Maximon, and Ouzo Bay are joining the lineup for Vino in Vogue, Harbor East’s signature wine tasting event. Sip and stroll your way through the neighborhood while sampling pours from renowned wineries. It’s an afternoon of fine wine, great food, and Harbor East energy you won’t want to miss.

October 3rd- 5th: The Choptank is making waves during the Annapolis Powerboat Show, one of the East Coast’s premier boating events. After exploring the latest yachts and powerboats on the water, head to The Choptank in Annapolis for fresh seafood, classic Maryland flavors, and unbeatable harbor views—the perfect way to cap off a day by the bay.

October 11th & 12th: Get ready for a neighborhood tradition—Fells Point Fun Fest is back, bringing live music, local vendors, and plenty of waterfront energy. While you’re here, make the most of the weekend at Atlas favorites throughout the neighborhood: sip and socialize at The Undefeated, enjoy classic Chesapeake flavors at The Choptank, catch the live music vibe at The Waterfront Hotel, and keep the celebration going at The Admirals Cup. Fells Point is the place to be all weekend long!

October 9th-12th: Set sail for the Annapolis Sailboat Show, where sleek yachts and classic sailboats line the harbor. After taking in the stunning views and nautical craftsmanship, drop by The Choptank to enjoy fresh seafood, Maryland favorites, and waterfront vibes that perfectly complement a day on the water. It’s the ultimate way to celebrate sailing season in Annapolis.

October 18th: Oystapalooza returns to Trolley Square Oyster House with $1 Buck-a-Shuck oysters from 12–8 p.m., live music and raffles from 1–6 p.m., and exclusive Dogfish and TSOH merch — including a limited-edition 2025 Oystapalooza T-shirt. Proceeds from the event benefit the Unlocke the Light Foundation.

October 25th: Get ready for some spook-tacular fun—The Valley Inn is hosting its very first Boo Brunch this Halloween! Little ghouls and goblins can enjoy kid-friendly activities, crafts, and games while parents dig into festive bites and seasonal treats. It’s a brunch full of tricks, treats, and all the Halloween magic you can handle—come in costume and join the fun!

October 25th: Mark your calendars and join us for The Choptank’s 5th Annual PAWty! Celebrate five years of tail-wagging fun with a costume contest, dog-friendly menu, and activities for our four-legged friends, while humans enjoy delicious bites and crush towers. It’s a paw-some tradition full of treats, tricks, and plenty of reasons to celebrate together!

October 30th: Join us for Monarque‘s second annual Halloween Cabaret! Prepare for a night celebrating the rich culture of New Orleans – mystical revelations, vampiric seduction, absinthe concoctions, and, of course, stimulating burlesque performances all night. For our dinner tickets, Chef Devin Parks will prepare his signature cuisine over five courses, and a sensory deprivation seance will transport you to a hedonistic experience like none other. Two craft cocktails will round out the experience – prepare to check your inhibitions at the door. Only interested in cocktails and a night of wild entertainment? Reserve your seat at the bar and we’ll provide two cocktails to tempt you into your darkest desires.