A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of February. Event dates may be subject to change.
2026 Chesapeake Fire & Ice Festival
Chesapeake Fire & Ice returns to downtown Easton for a vibrant, family-friendly winter celebration on Friday and Saturday, February 20–21, 2026. Presented by the Preston Automotive Group, this free festival transforms the town with stunning, larger-than-life ice sculptures, live music, seasonal shopping, and special restaurant and lodging offerings. Guests can enjoy interactive ice displays and fiery entertainment as Cascading Carlos returns with crowd-pleasing fire juggling performances at Thompson Park. The popular Fire Trail adds to the fun with warm drinks, tasty bites, tastings, and shopping throughout downtown, creating a festive atmosphere that showcases Easton at its winter best. Festival hours are Friday from 5:00 PM to 9:00 PM and Saturday from 11:00 AM to 8:00 PM. More info: discovereaston.com/fireandice
The 2026 Chesapeake Bay Boat Show
The Chesapeake Bay Boat Show returns to the Maryland State Fairgrounds Exhibition Hall in Timonium from February 5–8, 2026, bringing hundreds of boats and marine exhibitors together under one heated indoor roof. Explore sport fishing boats, cruisers, performance and ski boats, along with the latest marine gear and technology. The weekend also features fishing seminars, interactive exhibits, live music, food and drinks, and family-friendly activities, making it a great outing for seasoned boaters and curious newcomers alike. Show hours run Thursday (VIP Preview) 12–6 PM, Friday 10 AM–6 PM, Saturday 10 AM–7 PM, and Sunday 10 AM–4 PM. Free parking is available. More Info: thechesapeakebayboatshow.com
Casey Cares Sea of Hope Gala
Step into an evening of ocean-inspired elegance at the Casey Cares Sea of Hope Gala, a signature celebration supporting critically ill children and their families. Taking place February 21, 2026, from 6:30 to 11:00 pm at the American Visionary Art Museum in Baltimore, the night blends meaningful purpose with unforgettable style. Guests will enjoy a beautifully curated gala experience while helping fund Casey Cares’ uplifting programs that create joy, comfort, and lasting memories for families facing serious illness. The evening also honors this year’s Champion of Children Award recipients—donors whose generosity has made a profound impact on the organization’s mission. Co-chaired by Todd Travis and Robert Weltchek, the gala invites guests to dress in cocktail attire or black tie optional and be part of a night where compassion, community, and hope take center stage. More info: caseycares.org/event/gala/
Disney on Ice presents Frozen & Encanto
Disney On Ice brings the magic of Frozen and Encanto to life in an unforgettable family experience filled with music, movement, and dazzling performance. From Elsa’s icy world to the colorful rhythms of the Madrigal family, audiences are invited to sing along to beloved songs while watching world-class figure skating, breathtaking aerial acrobatics, and spectacular storytelling unfold on the ice. Disney On Ice presents Frozen & Encanto skates into Baltimore from February 5–8, 2026 at CFG Bank Arena, transforming the arena into a joyful celebration of courage, love, and imagination that delights fans of all ages. More info: https://www.disneyonice.com/en-us/jump-in-fairfax-baltimore/
Designer Purse BINGO (Benefiting Chesapeake K9 Fund)
Join us for an exciting evening of games, prizes, and giving back at Designer Purse BINGO on Friday, February 27, 2026, from 7:00 to 10:00 pm at the Severna Park Elks Lodge. This lively night combines classic BINGO fun with the chance to win stylish designer purses, all while supporting a meaningful cause. Proceeds from the event benefit the Chesapeake K9 Fund, a local 501(c)(3) organization dedicated to supporting first responder K9 units throughout the region. Your ticket includes admission, a door prize entry, and one pack of BINGO cards, with additional cards and daubers available for purchase at the event. Expect a festive atmosphere filled with food, drinks, friendly competition, and the satisfaction of knowing your participation helps protect and serve those who serve us. More info: stephanie@chesapeakek9fund.org
Photo Michael G. Stewart
Naptown Philharmonic: Legends and Landscapes
On Sunday afternoon, February 22, the Naptown Philharmonic Orchestra presents Legends and Landscapes at Maryland Hall, a dynamic concert blending music and movement in an unforgettable performance. Acclaimed pianist William Bloomquist takes center stage alongside expressive dancers from the Ballet Theatre of Maryland, bringing both sound and motion to life. Adding a meaningful local connection, talented musicians from Broadneck High School will perform side-by-side with members of the Naptown Philharmonic, creating a memorable community collaboration that highlights emerging and seasoned artistry together. With rich orchestral textures, captivating solo work, and spectacular dance elements woven throughout, this concert offers something truly special for music lovers and families alike. More info: naptownphil.org/
Scenic Rivers Winter Walk 2026
Experience the quiet beauty of winter on a guided, contemplative forest walk with Scenic Rivers Land Trust and Certified Forest Therapy Guide Laura Armstrong Falvey of Chesapeake Nature Connection. This two-hour experience takes place on Saturday, February 7, 2026, from 10:00 am to 12:00 pm at the Chesapeake Bay Foundation’s Philip Merrill Environmental Center, where participants will explore conserved woodland and shoreline trails through a mix of paved and unpaved paths. Using gentle, creative prompts, the walk encourages slowing down, engaging the senses, and connecting with nature in a peaceful, reflective setting. Open to ages 16 and up, this free event offers a serene way to appreciate winter’s unique charm, though space is limited and registration is required. More info: srlt.org/events
Naptown Flea Vintage & Vinyl
Discover a treasure hunter’s dream at the Naptown Flea, returning on February 1, 2026, at 11:00 AM at 801 Chase Street in Annapolis. This lively market brings together an eclectic mix of vintage finds and vinyl gems, offering everything from one-of-a-kind collectibles to records worth digging for. As you browse, enjoy sets from local DJs spinning throughout the day, adding the perfect soundtrack to your shopping experience. Come hungry—there will be delicious food on hand to fuel a full day of exploring, plus plenty of unbeatable deals you won’t want to miss. Whether you’re a serious collector or just love the thrill of the find, this is a can’t-miss event for anyone who appreciates vintage style, music, and local flavor. More info: www.instagram.com/naptownflea
Vanessa Collier At Rams Head on Stage
Vanessa Collier brings her powerful blend of soul, blues, and R&B to Rams Head On Stage on Saturday, February 14, 2026, with doors opening at 7:00 pm and the show starting at 8:00 pm. A four-time Blues Music Award winner, Collier is touring in support of her acclaimed sixth album, Do It My Own Way, a rich, analog-recorded collection inspired by classic Memphis soul and driven by fearless songwriting and standout musicianship. Known for her commanding vocals, saxophone prowess, and emotionally charged performances, Collier delivers a live show that’s both deeply personal and irresistibly groove-filled. Drawing influence from legends like Mavis Staples, Aretha Franklin, and James Brown, her music celebrates independence, resilience, and soulful storytelling. This all-ages concert promises an intimate, high-energy night with one of the most exciting voices in contemporary blues and soul. More info: ramsheadonstage.com
Annapolis Restaurant Week
Annapolis Restaurant Week 2025 runs for one delicious week, inviting locals and visitors to explore the city’s dynamic dining scene through specially curated prix fixe menus. Taking place from February 21 through March 1, 2025, this annual celebration features more than 30 participating restaurants showcasing their best dishes across breakfast, lunch, and dinner. It’s the perfect chance to try a new spot, revisit a longtime favorite, or enjoy a memorable meal in one of Annapolis’ historic or waterfront settings. With a wide range of cuisine styles and options for vegetarian and gluten-free diners, Restaurant Week highlights the creativity, flavor, and hospitality that make Annapolis a standout foodie destination—whether you’re dining out or enjoying your favorites at home. More info: annapolisrestaurantweek.com
Yarn & Pressing Strings
Yarn & Pressing Strings bring an electrifying night of roots-driven sound to the Avalon Theatre on Saturday, February 28, 2026, with doors opening at 6:30 pm and the show starting at 7:00 pm. This high-energy double bill pairs Yarn’s Americana-tinged alt-country—honed over more than a decade of national touring and shared stages with legends like Dwight Yoakam and Alison Krauss—with the soulful, genre-blending power of Annapolis favorites Pressing Strings. Led by Jordan Sokel, Pressing Strings fuse blues grit, folk warmth, and rock urgency into songs that are as emotionally rich as they are irresistibly danceable. The orchestra level will be general admission standing room with the dance floor open, while mezzanine and upper balcony seats offer reserved seating for those who prefer to take it all in from above. It’s a rare chance to catch two beloved bands in one unforgettable, party-ready night at one of the region’s most iconic venues. More info and tickets: avalontheatre.com
Love Stories To Tell in the Dark
Looking for a night that restores your faith in love? Head to Cult Classic on February 12 for an intimate, story-filled evening where local authors take the stage to share heartfelt, funny, and deeply human love stories. Each reader delivers a short 3–5 minute tale designed to spark connection, laughter, and maybe even a little hope, with doors opening to romance at 7:00 pm and the stories heating up at 7:30 pm. Grab a seat, settle in with a craft beer or fresh-made bite, and enjoy a cozy night of storytelling in a space known for good vibes and great company. Reserved seating is available in advance, with limited tickets at the door, so arriving early is encouraged. More info: www.cultclassicbrewing.com/#events
Explore the Shore Outdoor Expo
Set inside the beautifully restored Packing House, this one-day Outdoor Expo takes place on February 21 from 10:00am to 4:00pm and brings together outdoor brands, local businesses, and the community for an energetic celebration of adventure, skill, and Eastern Shore culture. Spend the day exploring hands-on gear demos, vendor exhibits, and informal clinics led by experienced outdoor experts, alongside live entertainment and family-friendly activities. Guests can sample craft food and beverages from local makers, enjoy a wild game culinary experience highlighting regional flavors, and connect with outfitters, guides, and conservation-minded organizations. The event also features an official Boone & Crockett and Pope & Young scoring and measuring opportunity, adding a unique draw for hunting and wildlife enthusiasts. It’s an immersive, laid-back day designed to inspire exploration and celebrate everything that makes outdoor life on the Shore special. More info: thepackinghousecambridge.com/outdoor-expo
