Mark your calendars for a season full of giving, celebration, and community spirit across Annapolis, the Eastern Shore, and Central Maryland.
From black-tie galas and waterfront festivals to family fun runs and heart-warming holiday traditions, our region knows how to pair celebration with giving back. This Winter and Spring, dozens of nonprofits are hosting can’t-miss events that not only bring our communities together but also raise vital support for causes close to home. Whether you’re looking to lace up your sneakers for a 5K, sample local flavors at a tasting, or dress up for a night of music and dancing, there’s something on this list for everyone. Browse through, save your favorites, and join in the spirit of generosity that makes our community shine.
Maryland Irish Festival
November 7th – 9th, 2025 | 12:00 PM – 11:00 PM, Benefiting Irish Charities of Maryland at Maryland state fairgrounds, More info: irishfestival.com
UM BWMC’s 60th Anniversary Gala
November 8th, 2025 | 6:30 PM – 11:00 PM, Benefiting Baltimore Washington Medical Center Foundation at Live! Casino, More info: umms.org
CASAblanca Gala
November 8th, 2025 | 6:00 PM – 11:00 PM, Benefiting Anne Arundel County CASA at Westin Annapolis Hotel, More info: facebook.com
Chase Brexton Annapolis Gala
November 8th, 2025 | 6:00 PM – 10:00 PM, Benefiting: Chase Brexton Health Care at Chesapeake Bay Foundation Headquarters, More info: chasebrexton.org
Bay Bridge Run
November 9th, 2025 | 7:00 AM – 1:00 PM, Benefiting: Chesapeake Conservancy, Severn Leadership Group & Walk the Walk Foundation at the Chesapeake Bay bridge, More info: thebaybridgerun.com
Sip & Savor
November 9th, 2025 | 1:00 PM – 4:00 PM, Benefiting Hospice of the Chesapeake at Newton White Mansion, More info: hospicechesapeake.org
A Celebration of Charities
November 13th, 2025 | 12:00 PM, Benefiting Chesapeake Charities at Chesapeake Bay Beach Club, More info: chesapeakecharities.org
Reelin' and Rockin' Rockfish Bash Benefit
November 13th, 2025 | 6:30 PM – 9:30 PM, Benefiting Lucky and Blessed Fishing, More info: rockfishbash.com
Waterfowl Festival
November 14th – 16th, 2025 | 10:00 AM – 4:00 PM, Benefiting William A. Perry Scholarship Fund & Samuel H. Shriver Jr. Sporting Heritage Fund in Downtown Easton, More info: waterfowlfestival.org
A Starry Night Fundraiser Gala
November 20th, 2025 | 6:00 PM – 10:00 PM, Benefiting Young Life at Fluegel Alumni Center at the U.S. Naval Academy, More info: ylaac. younglife.org
AACPL An Evening with David Baldacci
November 21st, 2025 | 6:30 PM, Benefiting AACPL Inc. at Chesapeake Arts Center, More info: chesapeakearts.org
Lights on the Bay
November 23rd, 2025 – January 1st, 2026 | 5:00 PM – 10:00 PM, Benefiting SPCA of Anne Arundel County at Sandy Point State Park, More info: lightsonthebaymd.org
Y Turkey Trot Charity 5K (Arnold)
November 27th, 2025 | 8:30 AM, Benefiting YMCA of Central Maryland – proceeds fund Y programs for families in need at The Y in Arnold, More info: runsignup.com
Festival of Trees – Kennedy Krieger
November 28th- 30th, 2025 | 8:00 AM, Benefiting Kennedy Krieger Institute at Kennedy Krieger Institute in Baltimore, MD., More info: kennedykrieger.org
Festival of Trees – Talbot Hospice
November 29th – December 1st, 2025 | 5:00 PM – 8:00 PM, Benefiting Friends of Hospice to benefit Talbot Hospice at The Gold Room of The Tidewater Inn, More info: festival-of-trees.org
Holiday Joy Gala
December 4th, 2025 | 5:00 PM, Benefiting Mid-Atlantic Symphony Orchestra at (TBD), More info: midatlanticsymphony.org
Lights of Kindness
December 5th, 2025 | 9:00 AM, Benefiting Rotary Club of South Anne Arundel County at Homestead Garden, More info: patch.com
UWLES 22nd Annual Holiday Ball
December 6th, 2025 | 6:00 PM, Benefiting United Way of the Lower Eastern Shore at Hyatt Regency Chesapeake Bay Resort & Spa in Cambridge, MD., More info: uwles.org
Annapolis Chocolate Binge Festival
December 7th – 9th, 2025 | 11:00 AM – 4:00 PM, Benefiting Inner West Street Association & Annapolis Arts District at the First block of West Street, More info: iwsannapolis.com
Nutcracker Tea
December 7th, 2025 | 10:00 AM – 5:00 PM, Benefiting Annapolis Holiday Traditions at DoubleTree Annapolis, More info: whatsupmag.com
Christmas in St. Michaels
December 12th – 14th, 2025 | Time TBD, Benefiting Local nonprofit organizations in Downtown St. Michaels, More info: christmasinstmichaels.org
Bay Bells & Shark Tails
December 13th, 2025 | 6:00 PM – 10:00 PM, Benefiting Core Shark H2O at Charles Carroll House, More info: csh2o.org
Holiday Book Festival
December 13th, 2025 | 11:00 AM – 4:00 PM, Benefiting Eastern Shore Writers Association at Cult Classic Brewing, More info: easternshorewriters.org
Atlantic General Hospital’s 32nd Annual Penguin Swim
January 1st, 2026 | 9:00 AM – 11:45 AM, Benefiting Atlantic General Hospital’s at Princess Royale Oceanfront Resort, More info: secure.qgiv.com
Polar Bear Plunge
January 23rd, 2026 | Time TBD, Benefiting Special Olympics Maryland at sandy point state park, More info: plungemd.com
Greater Maryland Heart Ball
February 6th, 2026 | 6:00 PM – 9:00 PM, Benefiting American Heart Association at M&T Bank Exchange, Baltimore, More info: ahabaltimore. ejoinme.org
Casey Cares Annual Gala
February 21st, 2026 | 6:30 – 11:00 PM, Benefiting Casey Cares at American visionary Art Museum, More info: caseycares.org
Southern Maryland Chapter Annual Fundraising Banquet
February 28th, 2026 | 6:00 PM – 9:30 PM, Benefiting Coastal Conservation Association at Calvert Marine Museum, More info: ccamd.org
Chefs for Habitat Gourmet Gala
March 7th, 2026 | Time TBD, Benefiting Habitat for Humanity at Wicomico Civic Center in Salisbury, MD, More info: chefsforhabitat.org
The Lighthouse Gala
March 7th, 2026 | 5:00 PM – 10:00 PM, Benefiting Lighthouse Christian Academy at TBD, More info: lcacademy.org
Black Tie & Diamonds
March 7th, 2026 | 6:00 PM – 10:00 PM, Benefiting Rotary Club of Annapolis at Annapolis Graduate Hotel, More info: annapolisrotary.org
Annapolis Film Festival
March 26th, 2026 | Time TBD, Benefiting Annapolis Film Festival at Ego Alley Annapolis, More info: zavros.place
Santé: Giving Back for Kidney Disease
March 26th, 2026 | Time TBD Benefiting National Kidney Foundation at Baltimore Museum of Industry, More info: kidney.org
Bubbles and Bingo
April 10th, 2026 | 6:00 – 11:00 PM, Benefiting Hospice of the Chesapeake at The Fluegel Alumni Center in Annapolis, More info: hospicechesapeake.org
The Blue-Ribbon Open House and Family Fun Day
April 11th, 2026 | 11:00 AM – 2:00 PM, Benefiting The Blue Ribbon Project at The Blue Ribbon Project, More info: blueribbonproject.org
Stronger Together Gala
April 25th, 2026 | 5:30 – 11:00 PM, Benefiting Unstoppable Joy at Oceans Downs Casino, More info: unstoppablejoyco.org
Walk for the Woods
May 2nd, 2026 | Time TBD, Benefiting Scenic Rivers Land Trust at (TBD), More info: srlt.org
Blue Ribbon Bash
May 16th, 2026 | Benefiting Blue Ribbon Project, at Severna Park Elks Lodge, More info: blueribbonproject.org
Submit Your Charity Event
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