Chesapeake Fire & Ice will again feature dozens of ice sculptures spread throughout Easton’s historic district.
From show-stopping live performances and soulful tributes to community celebrations and can’t-miss foodie events, this week’s lineup is packed with energy and variety. Catch imaginative young performers bringing fairytales to life, groove to iconic R&B duets, or enjoy a night of laughter for a great cause. Celebrate local sports excellence, sing along to Broadway favorites, get inspired at the Homeowners Expo, or stroll downtown with your pup during the Winter Pup Crawl. Add in poetry, Restaurant Week indulgence, a heartwarming SPCA dog walk, a vibrant Lunar New Year celebration, and powerful live songwriting, and you’ve got a week filled with culture, connection, and plenty of reasons to get out and experience something new.
Fairytales on Stage
February 18; Compass Rose Theater, Annapolis 5:30pm
Step into a world of imagination with Fairytales on Stage, an immersive ensemble theater program where students bring their own magical stories to life. Blending movement, dance, song, and drama, this creative experience invites young performers to explore character development and storytelling while crafting original fairytales inspired by both classic and contemporary fantasy. Guided by experienced instructors, students build confidence, collaboration skills, and artistic expression in a supportive, high-energy environment. The program culminates in a special presentation for family and friends, showcasing the imaginative worlds and characters created along the way. It’s a joyful celebration of creativity where wonder truly takes center stage.
Jazzy Blu Presents: Lovers & Legends: A Tribute to R&B's Greatest Duets
February 18th; Rams head On Stage, Annapolis 8:00pm
Celebrate the power of love and timeless music at Lovers & Legends: A Tribute to R&B’s Greatest Duets, presented by Jazzy Blu. Known as one of the Washington Metropolitan area’s premier Neo-Soul bands, Jazzy Blu delivers a smooth, groove-driven blend of R&B, jazz, funk, and soul that captures both heart and nostalgia. This special tribute highlights iconic duets that defined generations, pairing rich harmonies with the band’s signature emotional depth and dynamic stage presence. Having shared stages with Grammy Award-winning artists and performed at renowned venues across the country, Jazzy Blu brings polish, passion, and undeniable talent to every performance—making this an unforgettable night for R&B lovers of all ages.
Laugh for a Cause: Comics for Critters
February 19th; Federal House Bar & Grille, Annapolis 7:00pm
Join us for Comics for Critters, a stand-up comedy night benefiting the animals of the SPCA of Anne Arundel County. It’s an evening built for connection, laughter, and community — the kind of night that feels both fun and meaningful.
2026 Touchdown Club Football Awards Banquet
February 19th; the Westin Hotel, Annapolis 6:00pm
Celebrate the region’s top football talent at the 71st Annual Touchdown Club of Annapolis Football Awards Banquet. This special evening honors standout athletes from the U.S. Naval Academy, the University of Maryland, and Anne Arundel County, bringing together players, coaches, fans, and community leaders for a night of recognition and camaraderie. The event begins with a cocktail hour, followed by dinner and the awards presentation, all set in a business-attire atmosphere that reflects the prestige of the occasion. Guests will also hear from special guest speaker Brian Mitchell, former Washington Redskins Super Bowl Champion and NFL All-Pro running back, who will share insights from his legendary career. The celebration continues with an after-party, making this an unforgettable night dedicated to excellence on and off the field.
Live Arts Maryland Presents Broadway Favorites
February 20th; Maryland Hall, Annapolis 7:30pm
Live Arts Maryland marks America’s 250th birthday with a stirring musical tribute to the sounds that helped define a nation. This celebratory program features George Gershwin’s iconic Rhapsody in Blue, honoring his profound influence on the American songbook and the evolution of distinctly American music. The performance also shines a spotlight on beloved selections from Broadway, including highlights from Ragtime and Rodgers & Hammerstein’s Carousel. Joined by special guest artists and the Annapolis Chorale, this uplifting concert weaves together classical brilliance and theatrical charm in a powerful salute to America’s rich musical legacy.
The Home Owners Expo
February 21st – 22nd; The Byzantium Event Center, Annapolis 11:30am – 4:00pm
Get inspired at this year’s Homeowners Expo, a weekend packed with expert advice, practical tips, and special guest appearances designed to help you make the most of your home. Meet Richard Karn—Al Borland from Home Improvement—as he shares stories from the iconic sitcom and poses for photos, plus enjoy informative sessions on homeowner basics, spring tree care, Maryland’s Big Tree Program, and local resources like Makers Space Annapolis. All weekend long, “Ask a Master Gardener” offers the chance to get your plant and landscaping questions answered. Whether you’re planning projects or just looking for fresh ideas, this expo delivers insight and inspiration in one convenient place.
Winter Pup Crawl
February 21st; Downtown Annapolis, 11:00am
Bundle up and grab the leash—MD Pup Scouts is launching its first-ever Winter Pup Crawl, and it’s all about paws, people, and supporting local Annapolis businesses. Think bar crawl energy, but dog-friendly and way cuter. This community stroll takes you and your pup from stop to stop at participating local spots, where you’ll unlock special discounts, meet fellow dog lovers, and keep those tails wagging all winter long. It’s a fun, active way to explore downtown, connect with other pup parents, and turn an ordinary outing into a tail-wagging adventure.
Poets in the Conversation Room- Michael Gushue & Kim Roberts
February 21st; Francis Scott Key Auditorium, Annapolis 12:00pm
Experience the power of the written word at Poets in the Conversation Room, a vibrant literary series presented in partnership with Annapolis Home Magazine and St. John’s College. Hosted by renowned poet, playwright, and Maryland’s 10th Poet Laureate Grace Cavalieri, the series brings acclaimed voices together for engaging readings and conversation that celebrate poetry’s ability to move, challenge, and inspire. Cosponsored by Kymberly Taylor, Editor-in-Chief of Annapolis Home Magazine, this free program invites the community to gather and reconnect with an art form that speaks deeply to the human experience. Seating is first-come, first-served, and featured works will be available through the St. John’s College Greenfield Library and Bookstore.
Annapolis Restaurant Week
February 21st – March 1st; Downtown Annapolis
Gather your friends and family for a delicious celebration of food and wine as Annapolis Restaurant Week returns for another flavorful week of dining. This highly anticipated event showcases the city’s thriving culinary scene, inviting locals and visitors alike to explore special prix fixe menus, creative dishes, and signature favorites from participating restaurants throughout Annapolis. Whether you’re trying a new hotspot or revisiting a longtime favorite, it’s the perfect excuse to indulge, sip something special, and experience why Annapolis has become a true foodie destination.
2026 Chesapeake Fire & Ice Festival
February 20th – 21st; Downtown Easton
Chesapeake Fire & Ice transforms downtown into a sparkling winter wonderland filled with dazzling ice sculptures, lively entertainment, and festive energy. Dozens of intricately carved works from the artists at Icelab will line the historic district, creating the perfect backdrop for strolling, snapping photos, and soaking in the magic of the season. With music in the air and every icy masterpiece displayed outdoors, it’s an easy, enchanting way to experience the charm of town in winter. The celebration continues all weekend with an activity-filled Fire Trail, family-friendly fun, live entertainment, seasonal shopping and dining specials, and plenty of reasons to explore. From glowing fire features to creative ice artistry, it’s a vibrant community event that brings warmth and wonder to the heart of winter.
Stews and Brews
February 21st; Easton Volunteer Fire Department, Easton 12:00pm – 4:00pm
Shake off the chill at Stews & Brews, a flavorful winter celebration designed to be your cure for the winter blues. This lively tasting event brings together more than 25 craft brewers, wineries, and distillers, offering unlimited samples poured right into your commemorative tasting glass. From bold local beers to smooth spirits and regional wines, there’s something to warm every palate. Pair your sips with hearty bites as local restaurants and food trucks serve up comforting stews and chowders, creating the perfect cozy combination of rich flavors and good company. It’s a deliciously spirited way to gather with friends, explore new favorites, and toast your way through the season
SPCA's Hearts & Hounds
February 22nd; Annapolis Mall, Parole 8:00am
Start your morning with fresh air, wagging tails, and a little extra heart at Hearts & Hounds, a feel-good community dog walk benefiting the SPCA of Anne Arundel County. This uplifting event celebrates the heart-healthy benefits of having a dog while bringing animal lovers together for a relaxed, joyful stroll. Enjoy quality time with your pup, meet the SPCA’s mascot Lucky, and browse PAWS at the Mall for pet goodies and gifts—every purchase helping support animals in need. Join the fun on Sunday, February 22 from 8:00–10:00 AM at Annapolis Mall (entrance by Maggiano’s) and make it a morning that truly gives back.
LUNAR NEW YEAR CELEBRATION
February 22nd; St. Johns College, Annapolis 3:00pm
Ring in the Lunar New Year with a vibrant, high-energy cultural celebration featuring orchestra, choir, martial arts, acrobatics, and traditional dance performed by the renowned Art Troupe of Renmin University in Beijing. Comprised of exceptionally talented students ages 13–17, the troupe represents one of China’s most influential youth orchestras and choirs, blending artistic excellence with academic achievement. Presented by World Artists Experiences, a local nonprofit dedicated to bridging cultures through the arts, this dynamic performance offers a meaningful opportunity to experience the beauty, discipline, and spirit of Lunar New Year traditions. The celebration is free and open to the public on a first-come, first-served basis, making it an accessible and inspiring way to welcome the new year.
Ray Weaver
February 24th; Rams Head On Stage; Annapolis 8:00pm
Ray Weaver brings a powerful blend of honesty and heart to the stage, transforming deeply personal life experiences into songs that feel both intimate and universal. Praised by Rodney Crowell as an “important songwriter,” Weaver has earned a reputation for thoughtful, story-driven lyrics that raise awareness while striking an emotional chord with listeners. Often compared to storytelling greats like Steve Earle and Guy Clark, his music carries the weight of lived experience, delivered with sincerity and quiet strength. Expect an evening of compelling songwriting that lingers long after the final note.
