Events in Maryland & Pennsylvania
From the Great Frederick Fair, Westminster Fallfest, and the final Orioles homestand at Camden Yards to the Ravens home opener at M&T Bank Stadium, Ocean City's Oceans Calling and Country Calling festivals, the Fell's Point Fun Festival and Edgar Allan Poe Festival in Baltimore, the Annapolis Powerboat and Sailboat Shows, the National Apple Harvest Festival near Gettysburg, Hanover's Snack Town Fall Fest, and the Autumn Glory Festival out in the mountains of Western Maryland, there is always something happening across our region. Here is what's on over the next 30 days, curated by Nikki and the Shelley Home Group.
Showing events from September 16 through October 16, 2026 · Updated every Monday
September 16, 2026
The next few weeks are packed: the Great Frederick Fair runs September 18-26, Westminster Fallfest lands September 24-27, and the Orioles close out the regular season at Camden Yards September 18-23 while the Ravens host the home opener on September 20. Ocean City peaks with Oceans Calling September 25-27 and Country Calling October 2-3. Baltimore celebrates with the Fell's Point Fun Festival and Edgar Allan Poe Festival October 2-4, and the mountains of Western Maryland host the Autumn Glory Festival October 7-11. Plus the Annapolis boat shows, the National Apple Harvest Festival near Gettysburg, and family fall fun all month long.
Great Frederick Fair & Westminster Fallfest
Sep. 18 - 27 · Frederick & Westminster
225,000+ visitors at the fair, then Carroll's biggest family weekend
Orioles Final Homestand & Ravens Home Opener
September 18 - 23 · Baltimore
O's vs. Brewers & Blue Jays; Ravens vs. Saints on September 20
Ocean City Music Weekends
Sep. 25 - Oct. 3 · Ocean City
Oceans Calling then Country Calling on the beach
Baltimore Festivals & Autumn Glory
Oct. 2 - 11 · Baltimore & Oakland
Fell's Point Fun Festival, Poe Festival, then Autumn Glory in Deep Creek
Weekly producer-only farmers market with fresh local produce, baked goods, artisan crafts, and live music. A Saturday morning staple in downtown Westminster for over 30 years.
The main county farmers market at the Ag Center featuring local produce, meats, eggs, honey, baked goods, and artisan vendors from across Carroll County. The season wraps up with the Celebrating Fall market and Fall Marketplace on October 3.
Free Sunday evening concerts in Westminster. An easy way to wind down the weekend with live music and friendly faces from the community.
Weekly farmers market at Watkins Park with fresh local produce, baked goods, artisan crafts, and a friendly community atmosphere.
Sunday evenings with live music, free ice cream sundaes, and fireworks at Northside Park. A beloved Ocean City summer tradition for families.
A weekly lunchtime gathering of rotating food trucks serving diverse cuisines at Merriweather Row Plaza. A great midweek break in the heart of Columbia, running through the end of October.
Free live music every Friday evening at Rash Field Park with skyline and harbor views. A different act each week, from soul and gospel to indie and local bands. Bring a blanket and enjoy the sunset.
Enjoy free waterfront sunset concerts at the Maritime Museum every Thursday in September. Live music with stunning views of the creek as the season winds down.
Outdoor dining events on select evenings in downtown Annapolis with live music and the streets closed for al fresco dining. Runs Wednesdays through late September and Saturdays in October.
Free outdoor concert series at the Annapolis Town Center with live music from local and regional bands. Shop, dine, and enjoy live entertainment on Thursday evenings.
Free outdoor concerts at Quiet Waters Park featuring local bands in a beautiful waterfront setting. Bring blankets, chairs, and a picnic for a relaxing evening.
The O's interleague homestand! Catch the Baltimore Orioles host the Milwaukee Brewers for a weekend of baseball at Camden Yards. A perfect family outing.
Annual Greek festival featuring authentic Greek cuisine, live music, traditional dancing, church tours, and family-friendly activities. A Baltimore tradition celebrating Hellenic culture.
Fresh Chesapeake Bay oysters, live blues music, and craft brews on the Baltimore Peninsula waterfront. A delicious celebration of Maryland's culinary and musical heritage.
Baltimore's Big Dill Festival! A celebration of all things pickles and dill with food vendors, live music, craft cocktails, and pickle-themed fun at Power Plant Live! in the heart of the Inner Harbor.
The Ravens Home Opener! Lamar Jackson and the Baltimore Ravens host the New Orleans Saints at M&T Bank Stadium. A must-see for every Baltimore sports fan.
The final regular-season homestand at Camden Yards! Catch the O's host the Toronto Blue Jays, including home finale night on September 23. Do not miss the last regular-season games of the year in Baltimore.
Soul revivalists Thee Sacred Souls bring their warm, classic sound to the Pier Six waterfront with LA LOM and the M. Sisters opening. An evening of vintage R&B under the stars.
Award-winning Christian country vocalist Anne Wilson performs live at the historic Lyric Baltimore. A heartfelt, uplifting evening of music for the whole family.
The high-energy vocal ensemble Sainted Trap Choir brings its gospel-infused sound to the historic Lyric Baltimore for an uplifting night of music.
International soccer comes to Baltimore! Two of the Americas' biggest national teams, Colombia and Mexico, face off at M&T Bank Stadium in a marquee friendly. A huge night for soccer fans.
A friendly outdoor Oktoberfest in Federal Hill with beer, German food, polka music, kids games, and a community raffle. A relaxed way to celebrate the season in South Baltimore.
Baltimore's month-long citywide celebration of free arts and culture for National Arts & Humanities Month. Free concerts, museum admissions, performances, and exhibits at venues across the city all October long.
R&B soul man Raheem DeVaughn brings his smooth, romantic sound to the Baltimore waterfront at Pier Six Pavilion, with Daley opening. A perfect date-night concert.
The 60th annual Fell's Point Fun Festival draws 50,000+ visitors to the historic waterfront neighborhood! Food vendors, live music on multiple stages, artisan crafts, kids activities, and a classic Baltimore block-party atmosphere.
A celebration of Baltimore's favorite gothic son! Author talks, costumed tours, live readings, art, music, and Poe-themed programming at the legendary Westminster Hall. Great for curious older kids too.
The Smashing Pumpkins bring their Rats in a Cage Tour to CFG Bank Arena with all the hits and a spectacular arena production. A big night for alternative rock fans.
The Ravens return to M&T Bank Stadium to host the Tennessee Titans for an AFC showdown. Great Sunday football in Charm City.
A free, family-friendly Latino cultural festival during Hispanic Heritage Month with live music, dance, food, and the Parade of Latino Nations. A vibrant weekend in Patterson Park.
Synthwave favorites The Midnight bring their cinematic, retro-electronic sound to Rams Head Live in the Power Plant. A high-energy night of danceable nostalgia.
Indie rock stalwarts Modest Mouse perform live on the Baltimore waterfront with special guest Catherine Alexandra. A night of inventive, anthemic songwriting.
Baltimore-bred singer-songwriter Derrick Stroup performs live at the historic Lyric Baltimore for an evening of soulful, heartfelt original music.
A family fall carnival at the Timonium fairgrounds with the famous $1,000 Pumpkin Drop, oompah bands, live music, food, and kids activities. Adults $10, kids 12 and under free.
Legendary alternative rock band AFI brings their dark, anthemic sound to Rams Head Live in the Power Plant for an intense night of live music.
A Baltimore County fall tradition! Pick pumpkins, wander the corn maze, meet the farm animals, and enjoy fresh cider and donuts at Weber's Cider Mill Farm through the end of October.
Grammy-winning duo for KING & COUNTRY brings their spectacular, family-friendly live show to the historic Lyric Baltimore. A joyful evening of soaring pop and heartfelt songs.
A flagship family ice show! Beloved Disney characters come to life on the ice at CFG Bank Arena in Spotlight Magic. A magical outing for kids and kids at heart.
A classic Maryland fall farm tradition near Mt Airy with giant corn mazes, pumpkin picking, hayrides, farm animals, jump pillows, and seasonal treats. A favorite family outing on weekends through October.
Presented by Carroll County Public Library! Children's character breakfast, ticketed author events, book signings, author panels, and book sales for all ages.
Carroll County's largest family event! Carnival rides, games, a Kids Zone, bingo, scarecrow making, an art and craft show, and live music nightly. Features a Main Street parade Thursday at 7 PM with Making Waves, Amish Outlaws on Friday, and Weird Science on Saturday. Free admission and parking.
The annual corn maze opens at the Carroll County Ag Center for its fall season. Navigate through acres of cornfield maze, enjoy hayrides, and seasonal family fun on Friday, Saturday, and Sunday evenings. Also hosts Trunk or Treat on October 25.
The finale of Carroll County Beer Week! Sample pours from Maryland's best craft breweries on the historic grounds of Union Mills Homestead, with live music and fall flavors.
150+ vendors across the Ag Center grounds! The Carroll County Farmers Market celebrates fall while the Fall Marketplace fills the fairgrounds with handmade crafts, seasonal goods, food trucks, and fall family fun.
An intimate garden wine festival on the historic Carroll County Farm Museum grounds. Sample wines from regional wineries while strolling the fall gardens. A relaxing way to spend a Sunday.
Costas Colectivo brings Latin fusion sounds to Alive @ Five. The final September edition of this free weekly concert series by Carroll Creek.
Frederick County's single largest event attracting over 225,000 visitors! Carnival rides, livestock shows, grandstand concerts (including Daughtry on September 18), live entertainment, midway games, fair food, and exhibitions. A can't-miss fall tradition.
A lively brewery Oktoberfest at Prospect Point Brewing with craft beer, German-style food, live music, and festive fall vibes.
An authentic German-style Oktoberfest celebrating 25 years with German bands, Alpine dancers, polka, a Biergarten, children's tent, food and craft vendors across multiple stages. A festive start to October in Frederick.
The acclaimed vintage jazz band The Hot Sardines bring their irresistible sound to the Weinberg Center. A toe-tapping, family-friendly evening of music.
Bestselling humorist and storyteller David Sedaris brings his witty, sharp observations to the Weinberg Center for a night of laughter and reading.
One of the East Coast's largest juried arts-and-crafts festivals! Hundreds of artisans, live music, and food at the peak of fall color in Thurmont. A perfect leaf-peeping family weekend.
A beloved Howard County fall favorite with pumpkin picking, hayrides, farm animals, a petting zoo, and a giant corn maze. Open weekends from mid-September through November.
An outdoor evening at the Howard County Conservancy with local wine, beer, food, and live music set against the autumn gardens and historic barn.
Indie folk band Mt. Joy celebrates their 10th anniversary with a special headlining show at Merriweather Post Pavilion. A night of heartfelt songwriting and soaring harmonies.
Live music fills the historic streets of Ellicott City with multiple stages, local food, craft beverages, and a festive atmosphere in one of Howard County's most charming towns.
A vibrant celebration of Indian culture with music, dance, food, and family activities at the Howard County Fairgrounds. A colorful, welcoming weekend for the whole community.
Major music festival featuring 40+ indie and alternative acts across two stages at Merriweather Post Pavilion, including Mitski, Ethel Cain, Hayley Williams, MUNA, Brandi Carlile, and Rainbow Kitten Surprise. A huge weekend of live music in the heart of Howard County.
Howard County's craft beer and cider fall celebration with local breweries, live music, seasonal food, and family-friendly activities as autumn arrives.
Tour a stunning historic estate transformed by Howard County's top interior designers, landscapers, and artisans. A fundraiser that's equal parts inspiration and community.
A feel-good celebration of community, music, and social justice at Merriweather. Live performances, vendors, food, and family-friendly programming with a mission.
Hip-hop stars Logic and G-Eazy co-headline Merriweather with their Endless Summer Part II tour, with Juicy J along for the ride. A high-energy evening of bangers and hits for older teens and adults.
British indie-pop favorite beabadoobee brings her dreamy, nostalgic sound to Merriweather Post Pavilion with Wisp opening. A laid-back night of shimmering guitar pop.
The story of the Queen of Disco comes to life at Toby's Dinner Theatre. A high-energy musical celebrating Donna Summer's legendary career.
The 50th season of the Maryland Renaissance Festival! Jousting knights, artisan crafts, turkey legs, carnival rides, period entertainment, and family fun across 27 acres.
Five-time Grammy-winning blues guitarist Robert Cray performs live at Rams Head On Stage. A masterclass in blues guitar from a living legend.
A family-friendly beach festival featuring Little Feat, Yonder Mountain String Band, Bela Fleck, Sam Bush, and more, with stunning views of the Chesapeake Bay. Supports local conservation.
Beloved folk singer-songwriter Brett Dennen brings his warm, storytelling sound to Rams Head On Stage. An intimate evening of acoustic roots music.
An annual Annapolis tradition celebrating African American heritage and culture with live music, storytelling, art, food vendors, and family activities along the waterfront.
A lively street Oktoberfest in West Annapolis with craft beer, German food, live music, and family-friendly fun as the neighborhood closes its streets for the weekend.
Soulful singer-songwriter Victory Boyd performs live at Rams Head On Stage for an intimate evening of rich, gospel-tinged vocals.
Grammy-nominated country outlaw Margo Price performs live at Rams Head On Stage. A fiery evening of honky-tonk, soul, and storytelling.
The Buena Vista Orchestra brings the timeless Cuban sounds of the Buena Vista Social Club to Rams Head On Stage for a warm, joyful evening.
Free outdoor arts festival on historic West Street in Annapolis. Featuring 150+ local artists, live acoustic music, food trucks, and a vibrant community atmosphere.
The legendary North Mississippi Allstars bring their raw, hill-country blues-rock to Rams Head On Stage for a gritty, soulful night of live music.
The largest in-water powerboat show on the East Coast! 400+ boats, marine vendors, demos, and family fun along the Annapolis City Dock (Ego Alley). A great waterfront weekend.
The world's largest in-water sailboat show returns to the Annapolis City Dock! Hundreds of sailboats, seminars, and marine exhibits along the waterfront. A bucket-list weekend on the Bay.
Ballet Theatre of Maryland performs the classic romantic ballet La Sylphide at Maryland Hall. A beautiful evening of dance in the heart of Annapolis.
A spectacular display of colorful kites of all shapes and sizes filling the Ocean City sky. Kite-flying competitions, demonstrations, and family fun on the beach.
A craft beer celebration on the Ocean City bayside with unlimited tastings from 15+ local breweries, live music, food trucks, and vendors. A great reason to visit the shore this fall.
The Ocean City Chamber's annual all-you-can-eat Maryland crab feast with live music, vendors, and a great cause. A beloved shore tradition.
A massive three-day music festival on the Ocean City beach! Headlined by Dave Matthews Band, Twenty One Pilots, and Mumford & Sons, with Gwen Stefani, Hootie & the Blowfish, and 40+ artists across three stages. A can't-miss end-of-summer music weekend on the shore.
25+ country artists across three stages take over the Ocean City Inlet! Headliners include Chris Stapleton, Lainey Wilson, and Miranda Lambert. A huge country music weekend on the beach.
The 29th annual classic car show returns to Ocean City! Hundreds of vintage rides, live music, a vendors village, and family fun along the Boardwalk. A perfect fall shore weekend.
An autumn celebration at The Barn Resort with live music, seasonal food and drinks, hayrides, craft vendors, and family-friendly activities in the beautiful Adams County countryside.
A celebration of Adams County's diverse cultural heritage with live music, traditional crafts, ethnic foods, historical exhibits, and family activities at Gettysburg Rec Park.
Free fall tours of President Eisenhower's Gettysburg farm retreat, just outside the National Military Park. A wonderful, mellow history outing for all ages.
Two full weekends of apple-country fun! Crafts, food, live music, family entertainment, and dozens of apple treats at the South Mountain Fairgrounds near Biglerville. The perfect crisp-fall family day trip.
The 10th annual bowling takeover event in Hanover. A fun community gathering with bowling, games, food, and prizes for all ages and skill levels.
A high-energy tribute to Frankie Valli and The Four Seasons at the Eichelberger Performing Arts Center. Sing along to all the hits from a true American sound.
Hanover's fall celebration at Long Arm Reservoir with food trucks, craft vendors, kids and family activities, and live music. A fun day in the country for the whole family.
A tribute to the legendary music of Carole King and James Taylor at the Eichelberger Performing Arts Center. A warm, nostalgic evening for music lovers.
A free downtown Halloween celebration hosted by Main Street Hanover! Kids can trick-or-treat at participating shops in the heart of historic downtown Hanover. Fun for the whole family.
The 59th annual Autumn Glory Festival is Western Maryland's signature fall celebration! Five days of peak foliage, two grand parades (the Grand Feature Parade is Saturday, October 10), the Maryland State Banjo, Mandolin & Fiddle Championships, plus craft shows and family fun. Worth the drive to the mountains.
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