Downtown Cumberland offers a robust variety of events year-round. Check back often for updates!

Mastering your Natural Glow with Kimberly Weimer! Learn about makeup simplicity, proper placement, and a natural and polished look! Thursday, February 5 at 6:00 pm. RSVP only - 25 spots! Cash bar and light refreshments will be available.

Interested in sharpening your animal drawing skills? Drawing classes at The Arcadian Gallery are a great way to do that. In their new "How to Draw Animals" series, you'll start with human-like animals, then proceed to dogs, cats, horses, and more exotic animals. All of this will be under the instructive eye of Arcadian Gallery […]
A relaxed and creative evening at The Kensington in downtown Cumberland. Enjoy wine, light charcuterie-style bites and guided painting. Instruction by Beth Hiliker. All supplies provided. No artistic experience required - just come ready to sip, paint, snack and connect. Limited space - RSVP to Maranda Miller by February 2nd. 301-832-4894 or mmiller@kensington-evergreen.com

Opening of Awakening in Color: Explorations in Encaustic by Terri Yacovelli on Friday, February 6, 2026 at 6:00 pm. Followed by live concert with the band Bedford! Terri Yacovelli is a contemporary visual artist whose work explores inner landscapes through abstraction, color, and intuitive mark-marking. With a background in painting and education, her practice blends […]

Bedford ain't your daddy's rock band, but your dad would definitely crank them up in his Camaro. They present thoughtful lyric's delivered via soulful melodies, resting on a bed of energetic drums, moving bass and funky yet angry guitars. This 3 piece band with 2 lead singers isn't reinventing the wheel, but they will roll […]

Grab your favorites and enjoy an afternoon with us! Botox, rose bar, live DJ, and more!

Join Martha Macgill of Lily Books and philosopher and potter Jason Brady for a philosophical, classic analysis into how we choose to live the way to live with moral inquiry. This is a way to get what classic literature aims to explore. Why life matters! Book Discussion - Buddhism, Socrates and Ethics for an Uncertain […]

Join queer music scholar/musician Becks Lipshultz for a discussion on the practice of queer music in Appalachia and the history of queerness in county and americana music. Pay what you can - $5 suggested donation This event is being held in conjunction with Loft 129 and the Cumberland Pride Festival.

Becks is a queer scholar and musician, focusing their work on community engagement and placemaking through music and agriculture. As a musician, Becks works to create events that bridge the divisions in communities. Their scholarship focuses on queer Appalachian music and the importance that music traditions hold, both in Appalachian communities and the queer community. […]

If you are interested in social painting or drawing, please consider joining us! We will have a challenging still life set up for this first session. Bring your own supplies. Assistance will be available but no formal instruction. Space is limited, so call 240-916-8840 to make a reservation. Cost is $20 and wine is extra.

Music by DJ Racos. Show a text from your ex = $5 off axe throwing. Drink specials & hate throw happy hour.

From Canada to the stage at Loft 129...Lynne Hanson! Too tough for folk and too blues-influenced for country, Lynne Hanson's brand of porch music with a little red dirt can turn on a dime from a sunshine, blue sky ballad to a full on thunderstorm of gritty Americana swamp from one song to the next. […]

Celebrate love, music, and fine dining this Valentine's Day at Gallery Stage! Join us for an enchanting evening featuring a captivating performance by Rhinestones & Rust, set in the intimate and artful ambiance of the Ferleman Gallery. Dinner begins promptly at 6:00 pm | Concert at 7:00 pm Enjoy a gourmet buffet. Drinks available for […]

Valentine's Night, 7-9pm. Upside Down Hour. Singles & Couples Discounts. 80's Theme Line Dancing with DJ Racos & Melissa.

Love Stinks Let's Drink! Celebrate Valentine's Day at JZ's Pub on N. Centre! Music starts at 8:00 pm and karaoke at 9:00 pm!

Back again for Valentines Day - come yuck it up with the apple of your eye with another great line-up of the East Coast's best comics! This show features 5 fantastic comedians including the headliner Lisa Chimenti and feature comedians Lennon Free, Corey Bush, and Clarilee. The Show is hosted by local favorite Tate Griffin. […]

Join romance aficionado Theresa Vernot and get into the spirit of Valentine's weekend with a lively discussion of romance novels. Come and bring your favorite romance novel to share! Book Discussion - Born of the Night by Sherrilyn Kenyon Coffees, teas, specialty drinks and fresh goodies available for purchase.

Special Thursday show from a legendary Rocker! Mike Viola is a producer, musician, songwriter and singer. Viola may be best known for his work with Panic! at the Disco, Andrew Bird, Ryan Adams, Jenny Lewis, Fall Out Boy and Mandy Moore, but his solo career stands on its own starting with a number of acclaimed […]

Jackson Cole is a quickly rising East Coast talent in the rock genre, performing for audiences all over. A nominee for Best Songwriter in the 2023 Maryland Music Awards, Jackson is as much of a capable songwriter as he is a performer. Performing along the likes of National Acts like LA Guns, Great White, and […]

A Sci-Fi fantasy round-table on the popular Expanse Series. Join Cynthia Fenmore and Alice Wecker for a fun, other-worldly afternoon! Book - The Expanse Series - Book One, Leviathan Wakes

Ready to kick away the winter blues? Join the Arcadian Gallery on Wednesday, February 25 for their first pop-up chef experience, Arcadian X Yolo! The Arcadian Gallery hosts a South Pacific culinary celebration featuring rising star Yolo of Yolo Live Events and Yolo Catering. Reservations are required. Call 240-916-8840.

The Cash Out Show is an original and energetic tribute to the music of Johnny Cash and The Tennessee Three. Fronted by guitarist and singer Shawn Fogle, the band brings classic Cash songs to life-from the Sun Records era and Columbia hits to the later American Recordings-delivered with the raw, driving energy of Live at […]

Back again for 2026! Dance Party with all proceeds donated for the Hooley Plunge 2026! DJ Rob Zembower will be spinning all your favs with artists like TLC, Spice Girls, Nirvana, 2Pac, Britney Spears, NSYNC, Biggie, Mariah Carey, and more. Dress the part with 90s fashion like flannel shirts, band tees, chokers, butterfly clips, high-waisted […]

John women writers and poets for an amazing Friday evening and Saturday. A weekend open to all genders showcasing women authors and writers. Author readings, talks and writing workshops. More details coming soon! Mark your calendars!

Join the Allegany Museum and the Embassy Theatre for the third annual Murder at the Museum! Enjoy a night of mystery, savory treats, and fun. Each year they present a new whodunit - the twisty plot will be revealed when the show begins, so come prepared to solve the mystery! Each night, guests get a […]

Celebrate St. Patrick's Day at JZ's Pub! Stop by on your pub crawl for food specials, drink specials, and entertainment! Music starts at 8:00 pm and karaoke at 9:00 pm! JZ's will be open 7:00 pm to 12:00 pm on both Friday and Saturday!

Get Irish for the day at Downtown Cumberland's Annual Hooley Pub Crawl!

Showcasing Cumberland's authors as a legacy from The Book Centre and long-time owners Lee Schwartz and Gayle Griffiths. More details coming soon!

Roots-music shapeshifters Hackensaw Boys bring their famously high-energy, dance-floor-igniting live show to Gallery Stage. Bluegrass chops, folk-punk spirit, and the band's iconic handmade "charismo" percussion - this one's a full-body good time! Tickets are $20 and are available on Gallery Stage's website here: Hackensaw Boys Tickets

Friday, March 27th from 8:00 am to 1:00 pm. Held at the Cumberland Country Club. The "Like a Woman" event, hosted annually by the Chamber, is a dynamic and empowering gathering designed to celebrate and elevate women in business and leadership. This event provides a platform for women to network, share insights, and inspire each […]

Megan Jean returns to Gallery Stage for a special one-night performance, fresh off a fall residency at Gallery Stage that wrapped with a songwriter-style finale on December 11, 2025. Known for gutsy vocals, sharp lyricism, and a fearless blend of roots, rock, blues, and folk, Megan has spent nearly two decades on the road, building […]

Eli Lev is a Maryland-based singer-songwriter crafting heartfelt, uplifting folk/Americana. His intimate sound is rooted in lived experience and a deep sense of connection. Often compared to The Avett Brothers and The Lumineers, Eli is a powerful musical storyteller. Tickets are $20 and are available on Gellery Stage's website here:https://www.tickettailor.com/events/gallerystage/2015017

Ladies Night Out is an annual event hosted by the Allegany County Chamber of Commerce. Join them this year at Rocky Gap Casino Resort on Friday, April 10th at 6:00pm! Early Bird Tickets are available online! $55 per person. $400 for a table of 8. $500 for a table of 10. Tickets are available online […]

Buffalo Rose is a six-piece Pittsburgh band delivering joyful "Theatre Kid Americana." With sparkling harmonies, intricate acoustic arrangements, and heart-forward songwriting, their live show is vibrant, playful, and irresistibly fun. Come ready to sing along and leave smiling. Tickets are $20 and are available on Gallery Stage's website: https://www.tickettailor.com/events/gallerystage/2015056

Jenner Fox Band is a Bellingham, Washington-based group built on poignant storytelling, warm harmonies, and the quiet magic that happens when longtime collaborators truly listen to one another. Fronted by internationally touring songwriter Jenner Fox, the band blends humor, vulnerability, and conviction into songs that turn everyday moments into something quietly profound. Tickets are $20 […]

Minor Gold is a spellbinding duo featuring Tracy McNeil and Dan Parsons, whose partnership has evolved over nearly a decade. Built on gentle guitar, sparse textures, and haunting harmonies, their music is intimate, warm, and emotionally resonant. Minor Gold creates a hushed, deeply human listening-room experience. Tickets are $18 and are available here: https://www.tickettailor.com/events/gallerystage/2015131

The Close is a trio of introspective lyricists known for genre-blending melodies and rich harmonies. Their sound lives at the crossroads of country, folk/rock, and Americana with a pop sensibility that feels familiar yet fresh. Live, The Close creates an intimate experience that lingers long after the final song. Tickets are $20 and are available […]

Howard's Half Marathon/5K Run Festival is a charity event raising money for the Allegany County Animal Shelter, a municipal no-kill shelter located in Cumberland, MD and serving the surrounding area. Two events are featured - a half-marathon and a 5K race. Both courses are out and back format. Registration for each event begins on March […]
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