UPCOMING EVENTS
Second Saturdays in Downtown Cambridge
Join Cambridge Main Street for a special series of Second Saturdays, in Downtown Cambridge. Enjoy enhanced outdoor dining, shopping, gallery walks and LIVE music.
MUSICAL GUESTS:
Saturday, May 10: Guitars on Fire with Mike Elzey & Andy Fox. Special guests from Mike Elzey’s Guitar Studio from 5-8 p.m.
Saturday, June 14: NightCats from 6-9 p.m.
Saturday, July 12: DistilledGrace
Saturday, August 9: Chris Honeman
Saturday, September 13: The Sunset Riders Band
Saturday, October 11: Crushing Day
Saturday, November 8: Kentavius Jones at RaR Brewing
Thank You For Being a Friend
Picture it, Cambridge, Maryland, September 13, 2025 …
In celebration of the 40th Anniversary of the original date of one of the greatest shows in television history — launched on September 14, 1985 — which also starred a Cambridge resident of days gone by, Cambridge Main Street is putting a fun spin on September's Second Saturday.
Mark your calendars for “THANK YOU FOR BEING A FRIEND.”
We have visions of cocktails, cheesecake, palm trees, handbags and more.
LIVE MUSIC BY THE SUNSET RIDERS
Enjoy amazing harmonies by this band, hailing from Cecil County, Maryland. Street performance from 5-8 p.m.
COCKTAIL & CHEESECAKE CRAWL
Eat and drink your way through Downtown Cambridge for one of Cambridge Main Street’s signature themed crawls, featuring cocktails and cheesecake desserts, inspired by those four sassy ladies, that we all know and love! Crawl at your own pace and participating locations.
FOREVER GOLDEN COSTUME CONTEST
Dress like your favorite GG, strut your stuff and flaunt your best 80s costume jewelry for a chance to be crowned MOST GOLDEN by a panel of judges. Specific details to come.
For more information, email Christina@downtowncambridge.org.
BINGO WITH FRIENDS
If you are a fan of the OG GGs, or you just love a good game of BINGO, this will be a MUST-DO! All prizes will be GG themed AND, rumor has it, our friends at Blue Ruin will have some fun refreshments available, too!
Pre-registration is strongly recommended as we only have limited seating for the event.
TICKETS: https://forms.gle/rzWxz44ruM1HAETf7
Taste of Cambridge 2025
MARK YOUR CALENDARS FOR TASTE OF CAMBRIDGE 2025!
PURCHASE TICKETS HERE
Ticket holders will have exclusive access to “tastes” of each Cook-Off entry. Each ticket holder will also receive a ballot to cast a vote for the highly coveted PEOPLE’S CHOICE AWARD.
$50.00 Advance; $65.00 Day-Of
ANNOUNCING THIS YEAR’S COOK-OFF CATEGORIES:
Crab Cake
Seafood Soup or Stew
Crab Specialty
Eastern Shore Fare
(contains ingredients that can be caught or grown on the Shore)
Dessert
Cambridge Main Street is seeking participants for the
2025 Taste of Cambridge Cook-Off Competition.
INTERESTED IN BECOMING A VENDOR?
Spring Fling 2025
Spring Fling 2025
Featuring “Tastes of Main Street,” a curated menu, showcasing cuisine from a number of Cambridge eateries
Live music with Party Fowl Band
Silent Auction and Live Auction, with guest emcee, Shane Walker
Hearts on Main
Join us in Downtown Cambridge for a special Second Saturday, on February 8 — HEARTS ON MAIN!
LIVE music by the Solitude Road Band — the first in Cambridge Main Street’s Second Saturday Concert Series. Hosted by RaR Brewing, from 6-9 p.m.
Cupid’s Cocktail & Chocolate Crawl — Valentine’s themed cocktails and desserts, at a number of Downtown Cambridge eateries, beginning at 11 a.m. (availability based on establishment’s hours of operation).
Love Out Loud — Purchase a heart for someone special, which will be displayed in Downtown Cambridge from February 8-28. Hearts can be purchased HERE or by printing the order form, below, and returning to Christina@DowntownCambridge.org.
Hearts on Fire — Fire pits and s’mores, at Blue Ruin Plaza, from 4-7 p.m.
Mistletoe on Main
Cambridge Main Street is excited to invite the community to a Downtown Cambridge holiday EXPERIENCE on Saturday, December 14. We are working hard to make sure there is fun for your entire family.
Mark your calendars for MISTLETOE ON MAIN!!
Breakfast with Santa 9:00 a.m. Doors Open; 9:30 a.m.
Breakfast Dorchester Center for the Arts
Adults: $30.00; Children 10 and under: $15.00
(Advance tickets required)
The Christmas Shoppe on Poplar (Vendors) 11:30 a.m. - 4 p.m.
Christmas Cocktail Crawl
(Specialty holiday cocktails at various Downtown locations)Shop ‘Til You Drop Promotion
(See list of participating businesses)Pet Pictures with Santa 11:30 a.m. - 1 p.m.
$10.00 each (Proceeds donated to Baywater Animal Rescue & Dorchester County Dog Control)Caricature Artist 1 p.m. - 5 p.m.
(Drawings available for purchase for $15 each)Christmas Caroling
Photo Booth
Letters to Santa Station
~ SNOW ~
Taste of Cambridge
Taste of Cambridge returns for its 16th year on Saturday, October 12, from 12pm to 6pm. Celebrate the best of Eastern Shore cuisine with Cambridge Main Street’s premiere community street festival.
TICKETS ARE ON SALE NOW!
Advance Tickets: $50.00; Day-Of Event Purchase: $65.00
Fiddle Jam @ The Farmers Market
The Fiddle Jam trio is an old-time string band that focuses on instrumental music ("fiddle tunes"). Its members are Dave Moore (banjo and guitar), Beth Roesel (fiddles), and Phil Toussaint (mandolin and guitar).
Fiddle Jam @ The Farmers Market
The Fiddle Jam trio is an old-time string band that focuses on instrumental music ("fiddle tunes"). Its members are Dave Moore (banjo and guitar), Beth Roesel (fiddles), and Phil Toussaint (mandolin and guitar).
AMPERSAND @ The Farmers Market
Ampersand’s members (Beth Lawton, Dick Hogle, Topher Lawton, and Dave Moore) bring guitars, mandolin, bouzouki, hammered dulcimer, mountain dulcimer, banjo, bass, cello, penny whistles, and percussion to support rich vocal harmonies and great joy in bringing traditional Americana music to modern audiences. Based in Easton, MD, this group shares an interactive program of songs and tunes from colonial America, to the Civil War era, blues of the 1920s and 30s, and on up to modern folk music. Details and links to their albums on Spotify can be found at their website: www.ampersandmusic.org.
Eagleman Beer Truck
Eagleman Beer Truck
The Cambridge Main Street beer truck will be open for business on Sunday, June 9 from 9am-the end of the race at Gerry Boyle Park. Stop on by to say hi 👋 and grab a cold one 🍺! All proceeds raised from the beer truck go to support Cambridge Main Street operating expenses.
AMPERSAND @ The Farmers Market
Ampersand’s members (Beth Lawton, Dick Hogle, Topher Lawton, and Dave Moore) bring guitars, mandolin, bouzouki, hammered dulcimer, mountain dulcimer, banjo, bass, cello, penny whistles, and percussion to support rich vocal harmonies and great joy in bringing traditional Americana music to modern audiences. Based in Easton, MD, this group shares an interactive program of songs and tunes from colonial America, to the Civil War era, blues of the 1920s and 30s, and on up to modern folk music. Details and links to their albums on Spotify can be found at their website: www.ampersandmusic.org.
