Photo By Mike Leubecker
What To Know Before You Go: Maryland Renaissance Festival
brEach year the Maryland Renaissance Festival’s Village of Revel Grove comes to life in the forests and glen of Crownsville. The countryside is transformed with more than 200 entertainers making merry amongst the 16th century shops, emporiums, and eateries of King Henry VIII’s magical kingdom. Read on for details >>
The What's Up? Weekend Rundown
Annapolis
Ladies Night Out
brThursday, September 21st, 4 p.m. (restaurants) & 5 p.m. (stores)
brLong-standing business owners will join with their new neighbors and business owners for a series of events including Ladies Night Out! Women-owned small businesses, One Petticoat Lane, Wrabyn, Excel Pilates Annapolis, Mexican Café, Cottonseed Glory, West Annapolis Art Works, Jackie’s Design Hair & Skin Studio, and Better Homes and Gardens, the J. Melvin group will all host unique specials. Plus Flamant, Evelyn’s Café, and Bon Vivant Antiques & Period Furnishings will all be participating. Ladies Night Specials Include an art show opening, discounted drinks and food, raffles, demonstrations, discounted apparel, and so much more!
An Evening with Randy Newman
Thursday, September 21st, 8 p.m.
brWith songs that run the gamut from heartbreaking to satirical and a host of unforgettable film scores (The Natural, Awakenings, all three Toy Story pictures, Seabiscuit, James and the Giant Peach, A Bug’s Life, Monsters Inc., and more), Randy Newman has used his many talents to create musical masterpieces widely recognized by generations of audiences. Among Randy Newman’s many honors are six Grammy Awards, three Emmys, and two Academy Awards, as well as a star on the Hollywood Walk of Fame. He was inducted into the Songwriters Hall of Fame in 2002 and the Rock and Roll Hall of Fame in 2013.
SAP 2017 International 505 World Championships
brThursday, September 21st through Friday, September 29th, times vary
brInternational 5O5 sailors, and their boats, converge in Annapolis for the 2017 SAP International 5O5 World Championship at Severn Sailing Association and Eastport Yacht Club. Competitors are expected from Australia, Bermuda, Canada, Japan, Germany, Great Britain, Ireland, France, Sweden, Denmark, Poland, and the U.S. This is the 62nd running of the 5O5 World Championship and the first time the Chesapeake Bay area has hosted this event. SAP has been the Title Partner of the event since 2009 and provides a robust viewer experience through live programming and their SAP Sailing Analytics app.
Maryland Renaissance Festival
brWith songs that run the gamut from heartbreaking to satirical and a host of unforgettable film scores (The Natural, Awakenings, all three Toy Story pictures, Seabiscuit, James and the Giant Peach, A Bug’s Life, Monsters Inc., and more), Randy Newman has used his many talents to create musical masterpieces widely recognized by generations of audiences. Among Randy Newman’s many honors are six Grammy Awards, three Emmys, and two Academy Awards, as well as a star on the Hollywood Walk of Fame. He was inducted into the Songwriters Hall of Fame in 2002 and the Rock and Roll Hall of Fame in 2013.
SAP 2017 International 505 World Championships
brThursday, September 21st through Friday, September 29th, times vary
brInternational 5O5 sailors, and their boats, converge in Annapolis for the 2017 SAP International 5O5 World Championship at Severn Sailing Association and Eastport Yacht Club. Competitors are expected from Australia, Bermuda, Canada, Japan, Germany, Great Britain, Ireland, France, Sweden, Denmark, Poland, and the U.S. This is the 62nd running of the 5O5 World Championship and the first time the Chesapeake Bay area has hosted this event. SAP has been the Title Partner of the event since 2009 and provides a robust viewer experience through live programming and their SAP Sailing Analytics app.
Maryland Renaissance Festival
Saturday, September 23rd & Sunday, September 24th 10 a.m. –7 p.m.
brThe region’s premier outdoor event and second largest Renaissance Festival in the country is celebrating its 41st season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. A playground of fun, frivolity, and wondrous performances thrill more than 300,000 visitors each year. The almost continuous entertainment on all 10 stages features many returning favorite performers! Music fills the village, from sea chanties to Celtic drums, you’ll move to the rhythm of more than 100 musical performers.
28th Annual Kunta Kinte Heritage Festival
brThe region’s premier outdoor event and second largest Renaissance Festival in the country is celebrating its 41st season at Revel Grove. Travel back in time as you immerse yourself in the culture of a 16th-century English village, complete with King Henry VIII and his court. A playground of fun, frivolity, and wondrous performances thrill more than 300,000 visitors each year. The almost continuous entertainment on all 10 stages features many returning favorite performers! Music fills the village, from sea chanties to Celtic drums, you’ll move to the rhythm of more than 100 musical performers.
28th Annual Kunta Kinte Heritage Festival
Saturday, September 23rd, 10 a.m. –7 p.m.
brCome enjoy live music & dance performances, world foods & artisan vendors, as well as heritage & history along the Downtown Annapolis waterfront! Kids can enjoy the children’s activity tent providing an interactive arts and crafts experience. The Kunta Kinte Heritage Festival is a free, family-friendly celebration of the perseverance, education, and cultural heritage of people of African descent.
Seventh annual Singable Feast
brSaturday, September 23rd, 6 p.m. –11 p.m.
brCelebrate with the Annapolis Opera at the 45th season opening celebration, the Singable Feast. This celebration is an unforgettable gala evening of fine dining, live and silent auctions, which include trips and unique experiences, and a raffle to win a cruise for two. The highlight of the evening will be a concert featuring two rising opera artists, Leah Hawkins, soprano and Matthew White, tenor, performing favorite works.
Jeffrey Osbourne
brSaturday, September 23rd, 8 p.m.
brJeffrey Osborne is the five-time Platinum and Gold Record winner who gave us such indelible hits as “Stay With Me Tonight”, “Only Human” and of course “On The Wings Of Love”.brNo other artist has made a singular impression on contemporary and popular music quite like Jeffrey Osborne. If you’re a lover of music, you won’t want to miss this legend live – who after more than four decades is better than he’s ever been!
Annapolis Run for The Light House
brCome enjoy live music & dance performances, world foods & artisan vendors, as well as heritage & history along the Downtown Annapolis waterfront! Kids can enjoy the children’s activity tent providing an interactive arts and crafts experience. The Kunta Kinte Heritage Festival is a free, family-friendly celebration of the perseverance, education, and cultural heritage of people of African descent.
Seventh annual Singable Feast
brSaturday, September 23rd, 6 p.m. –11 p.m.
brCelebrate with the Annapolis Opera at the 45th season opening celebration, the Singable Feast. This celebration is an unforgettable gala evening of fine dining, live and silent auctions, which include trips and unique experiences, and a raffle to win a cruise for two. The highlight of the evening will be a concert featuring two rising opera artists, Leah Hawkins, soprano and Matthew White, tenor, performing favorite works.
Jeffrey Osbourne
brSaturday, September 23rd, 8 p.m.
brJeffrey Osborne is the five-time Platinum and Gold Record winner who gave us such indelible hits as “Stay With Me Tonight”, “Only Human” and of course “On The Wings Of Love”.brNo other artist has made a singular impression on contemporary and popular music quite like Jeffrey Osborne. If you’re a lover of music, you won’t want to miss this legend live – who after more than four decades is better than he’s ever been!
Annapolis Run for The Light House
Sunday, September, 24th, 8 a.m.
brThe Friends of The Light House will host the Annapolis Run For The Light House Half Marathon (8 a.m.), Joggin Joe Shafran Memorial 5K Run (8:45 a.m.), and the 1.25 Dash for Donuts/Walk (9 a.m.) at Quiet Waters Park. The Dash for Donuts/Walk and 5K routes will follow the scenic trails inside Quiet Waters Park and the half marathon route will continue through the beautiful waterfront community of Hillsmere Shores. Registration includes $50 for the 5K, $90 for the half marathon, and $25 for the 1.25-mile dash. All proceeds from the event will benefit The Light House: A Homeless Prevention Support Center in Annapolis.
27th Annual West Annapolis Oktoberfest
brSunday, September 24th, 10 a.m. –5 p.m.
brThis long-standing Annapolis street festival will include traditional German food, beer and music from the crowd pleasing Oom-pa-pa Band. Attendees will find more than 130 arts, crafts and food vendors selling everything from bratwurst to fine art, roast beef to jewelry, and many West Annapolis clothing, antique, framing, craft and gift stores will be open for business. This is a family friendly event includes a moon bounce, body painting, and picnic tables for lovely outdoor dining.
Out of the Darkness Walk
brSaturday, September 23rd, 9 a.m.
brSuicide prevention starts with everyday heroes like you. Join the walk to fight suicide and help raise awareness about mental health. Be a part of the movement turning hope into action and create a culture that’s smart about mental health. Funds raised at the walks will benefit the American Foundation for Suicide Prevention. There will be memorial activities to honor loved ones and resource tables to visit before and after the walk.
Music & Art in the Park
brSaturday, September 23rd, 10 a.m. – 4 p.m.
brCome support the Stevensville Arts & Entertainment District’s annual event bringing awareness to The Mcardle School, Center for Early Childhood Autism Intervention, which are both non-profits sharing the proceeds. Enjoy a fall atmosphere with a hometown vibe showcasing local artists and their masterpieces, plus live music by The Island!
Layton's Chance Harvest Festival and Vineyard Dash
Saturday, September 23rd, 10 a.m.
brJoin this daylong celebration of the end of the Harvest season at Layton’s Chance Vineyard and Winery. Kick off the day with a scenic trail-run through the vineyards in the Vineyard Dash 5K! Immediately following the race will be the eighth annual Harvest Festival. There will be plenty of things to do for the adults and kids a like. Food and craft vendors, hayrides, pony rides, agricultural demonstrations, grape stomping, moon bounce, and so much more!
CBMM’s Family Day
brThe Friends of The Light House will host the Annapolis Run For The Light House Half Marathon (8 a.m.), Joggin Joe Shafran Memorial 5K Run (8:45 a.m.), and the 1.25 Dash for Donuts/Walk (9 a.m.) at Quiet Waters Park. The Dash for Donuts/Walk and 5K routes will follow the scenic trails inside Quiet Waters Park and the half marathon route will continue through the beautiful waterfront community of Hillsmere Shores. Registration includes $50 for the 5K, $90 for the half marathon, and $25 for the 1.25-mile dash. All proceeds from the event will benefit The Light House: A Homeless Prevention Support Center in Annapolis.
27th Annual West Annapolis Oktoberfest
brSunday, September 24th, 10 a.m. –5 p.m.
brThis long-standing Annapolis street festival will include traditional German food, beer and music from the crowd pleasing Oom-pa-pa Band. Attendees will find more than 130 arts, crafts and food vendors selling everything from bratwurst to fine art, roast beef to jewelry, and many West Annapolis clothing, antique, framing, craft and gift stores will be open for business. This is a family friendly event includes a moon bounce, body painting, and picnic tables for lovely outdoor dining.
Eastern Shore
Out of the Darkness Walk
brSaturday, September 23rd, 9 a.m.
brSuicide prevention starts with everyday heroes like you. Join the walk to fight suicide and help raise awareness about mental health. Be a part of the movement turning hope into action and create a culture that’s smart about mental health. Funds raised at the walks will benefit the American Foundation for Suicide Prevention. There will be memorial activities to honor loved ones and resource tables to visit before and after the walk.
Music & Art in the Park
brSaturday, September 23rd, 10 a.m. – 4 p.m.
brCome support the Stevensville Arts & Entertainment District’s annual event bringing awareness to The Mcardle School, Center for Early Childhood Autism Intervention, which are both non-profits sharing the proceeds. Enjoy a fall atmosphere with a hometown vibe showcasing local artists and their masterpieces, plus live music by The Island!
Layton's Chance Harvest Festival and Vineyard Dash
Saturday, September 23rd, 10 a.m.
brJoin this daylong celebration of the end of the Harvest season at Layton’s Chance Vineyard and Winery. Kick off the day with a scenic trail-run through the vineyards in the Vineyard Dash 5K! Immediately following the race will be the eighth annual Harvest Festival. There will be plenty of things to do for the adults and kids a like. Food and craft vendors, hayrides, pony rides, agricultural demonstrations, grape stomping, moon bounce, and so much more!
CBMM’s Family Day
Saturday, September 23rd, 10 a.m. –2 p.m.
brThe public is invited to Family Day at the Chesapeake Bay Maritime Museum in St. Michaels! Guests can follow a special Quest Card to explore family-friendly exhibits and enjoy hands-on activities along CBMM’s 18-acre campus. Families can examine the critters living on an oyster reef, learn to take photos like Robert de Gast, and help construct a dugout canoe. Guests can dress as a lighthouse keeper and explore what life was like for those who worked in the 1879 Hooper Strait Lighthouse, before climbing to the top for a bird's-eye view.
Concours d' Elegance 2017
brSunday, September 24th, 10 a.m.
brAfter nine years, the 11th annual St. Michaels Concours d’ Elegance returns to the waterfront lawn of the world class Inn at Perry Cabin. Peruse rare exquisite rolling works of art including pre-war coach-built and award-winning sports cars. Like the traditional events held in Paris, the show field is complemented with an elegant fashion show. An enhanced VIP Lounge and garden party exclusively offers culinary delights, libations, and live music. Enjoy a day of grand classic motoring, antique wooden speedboats, fashion, and style. Proceeds benefit the new Classic Motor Museum.
The Drag Race-Men in Heels
brSunday, September 24th, 2 p.m.
brGet ready for some fun when Washington Street turns into a race track for some of the area’s well known men. These good-natured guys are going to be looking “uptown” as they put on a pair of ladies high heels and race through “downtown” Easton! It’s all in good fun and being done to raise money for the Friends of Hospice event held annually in November.
Seventh Annual Mermaid’s Kiss Oyster Fest
brThursday, September 21st, 6 p.m.–10 p.m.
brJoin a night of all-you-can eat oysters, fresh seafood dishes from iconic and up-and-coming restaurants, and live entertainment as we raise funds to build a better Chesapeake Bay. This year’s event will feature a Bay-themed silent auction, one-of-a-kind oyster sculpture by the Chesapeake Mermaid, prizes, giveaways, and more!
Wine & Wag
brThe public is invited to Family Day at the Chesapeake Bay Maritime Museum in St. Michaels! Guests can follow a special Quest Card to explore family-friendly exhibits and enjoy hands-on activities along CBMM’s 18-acre campus. Families can examine the critters living on an oyster reef, learn to take photos like Robert de Gast, and help construct a dugout canoe. Guests can dress as a lighthouse keeper and explore what life was like for those who worked in the 1879 Hooper Strait Lighthouse, before climbing to the top for a bird's-eye view.
Concours d' Elegance 2017
brSunday, September 24th, 10 a.m.
brAfter nine years, the 11th annual St. Michaels Concours d’ Elegance returns to the waterfront lawn of the world class Inn at Perry Cabin. Peruse rare exquisite rolling works of art including pre-war coach-built and award-winning sports cars. Like the traditional events held in Paris, the show field is complemented with an elegant fashion show. An enhanced VIP Lounge and garden party exclusively offers culinary delights, libations, and live music. Enjoy a day of grand classic motoring, antique wooden speedboats, fashion, and style. Proceeds benefit the new Classic Motor Museum.
The Drag Race-Men in Heels
brSunday, September 24th, 2 p.m.
brGet ready for some fun when Washington Street turns into a race track for some of the area’s well known men. These good-natured guys are going to be looking “uptown” as they put on a pair of ladies high heels and race through “downtown” Easton! It’s all in good fun and being done to raise money for the Friends of Hospice event held annually in November.
Western Shore
Seventh Annual Mermaid’s Kiss Oyster Fest
brThursday, September 21st, 6 p.m.–10 p.m.
brJoin a night of all-you-can eat oysters, fresh seafood dishes from iconic and up-and-coming restaurants, and live entertainment as we raise funds to build a better Chesapeake Bay. This year’s event will feature a Bay-themed silent auction, one-of-a-kind oyster sculpture by the Chesapeake Mermaid, prizes, giveaways, and more!
Wine & Wag
Friday, September 22nd, 5:30 p.m. –8 p.m.
brThis event will feature a wading pool for pets, fun runs, bobbing for hot dogs, and paw painting for dogs. The "Flea-less" Market, a make-your-own donation pet supply yard sale, is back again by popular demand. There will also be cold beer, wine, soft drinks, and food by local vendors.
Ride for the Rivers & Muddy Bottom BBQ
brSaturday, September 23rd, 8 a.m. –3 p.m.
brThe Fourth annual Ride for the Rivers & Muddy Bottom BBQ is a Metric Century Bicycle Ride, a 40-Mile Ride, Family Fun Ride, followed by a great BBQ to benefit the West & Rhode Riverkeeper. Discover the beauty of the watersheds of the West and Rhode Rivers (as well as the Patuxent River and Herring Bay), on this challenging ride through the rolling countryside of Southern Anne Arundel County and Northern Calvert County. Proceeds help the West & Rhode Riverkeeper keep these rivers swimmable, fishable, crab-able and kayak-able.
Main Street Music Fest
brThis event will feature a wading pool for pets, fun runs, bobbing for hot dogs, and paw painting for dogs. The "Flea-less" Market, a make-your-own donation pet supply yard sale, is back again by popular demand. There will also be cold beer, wine, soft drinks, and food by local vendors.
Ride for the Rivers & Muddy Bottom BBQ
brSaturday, September 23rd, 8 a.m. –3 p.m.
brThe Fourth annual Ride for the Rivers & Muddy Bottom BBQ is a Metric Century Bicycle Ride, a 40-Mile Ride, Family Fun Ride, followed by a great BBQ to benefit the West & Rhode Riverkeeper. Discover the beauty of the watersheds of the West and Rhode Rivers (as well as the Patuxent River and Herring Bay), on this challenging ride through the rolling countryside of Southern Anne Arundel County and Northern Calvert County. Proceeds help the West & Rhode Riverkeeper keep these rivers swimmable, fishable, crab-able and kayak-able.
Main Street Music Fest
Saturday, September 23rd, 12 p.m.
brThe sixth edition of the Main Street Music Fest has become known since its inception as a marquee festival for independent and unsigned bands, providing them exposure to thousands of attendees. This year’s festival will feature over 50 bands on six stages, with music starting at 12 p.m. Lionize, Kelly Bell Band, The Henchmen, RÊVE and Victims of Experience are confirmed for headlining slots this year. Also announced for the festival: The Last Year, Sons of the Radio, Smantx. and Soul Island Rebels. The festival fun goes beyond great music, with local craft beer and wine offerings, food from local restaurateurs on offer, vendors of all kinds featuring many unique items, and the always-popular Star Wars Village.
The National Capital Radio & Television Museum Fourth Annual Fall Fundraiser Gala
brThe sixth edition of the Main Street Music Fest has become known since its inception as a marquee festival for independent and unsigned bands, providing them exposure to thousands of attendees. This year’s festival will feature over 50 bands on six stages, with music starting at 12 p.m. Lionize, Kelly Bell Band, The Henchmen, RÊVE and Victims of Experience are confirmed for headlining slots this year. Also announced for the festival: The Last Year, Sons of the Radio, Smantx. and Soul Island Rebels. The festival fun goes beyond great music, with local craft beer and wine offerings, food from local restaurateurs on offer, vendors of all kinds featuring many unique items, and the always-popular Star Wars Village.
The National Capital Radio & Television Museum Fourth Annual Fall Fundraiser Gala
Saturday, September 23rd, 6:30 p.m. –10 p.m.
brThe National Capital Radio & Television Museum hosts its fourth annual Fall Fundraiser and Gala. There will be a special raffle as well as a silent auction. The event this year will also celebrate the career of Washington, DC’s entertainment reporting icon, Arch Campbell, and his lifelong contributions to broadcasting with the Ed Walker Lifetime Achievement in Broadcasting Award.
Fifth annual Bull and Oyster Roast Fundraiser
brThe National Capital Radio & Television Museum hosts its fourth annual Fall Fundraiser and Gala. There will be a special raffle as well as a silent auction. The event this year will also celebrate the career of Washington, DC’s entertainment reporting icon, Arch Campbell, and his lifelong contributions to broadcasting with the Ed Walker Lifetime Achievement in Broadcasting Award.
Fifth annual Bull and Oyster Roast Fundraiser
Saturday, September 23rd, 7 p.m. –11 p.m.
brLots of great food, dancing, raffles, and door prizes! Join this fun filled evening in support of Special Olympics Anne Arundel County athletes participating in a variety of competitive sports year-round. Please visit the Special Olympics Anne Arundel County website for additional information.
An Evening with Alison Krauss & David Gray
brSaturday, September 23rd, 8 p.m.
brAlison Krauss’ new album Windy City is her first effort away from her band Union Station since Raising Sand and her debut for Capitol Records. The album features 10 classic songs that she carefully selected. 21 years since his first studio album, David Gray's tenth and latest, "Mutineers," finds the singer-songwriter steering into unfamiliar territory while cultivating a pugnacious, but respectful relationship with his own history.
WPOC Sunday in the Country
brLots of great food, dancing, raffles, and door prizes! Join this fun filled evening in support of Special Olympics Anne Arundel County athletes participating in a variety of competitive sports year-round. Please visit the Special Olympics Anne Arundel County website for additional information.
An Evening with Alison Krauss & David Gray
brSaturday, September 23rd, 8 p.m.
brAlison Krauss’ new album Windy City is her first effort away from her band Union Station since Raising Sand and her debut for Capitol Records. The album features 10 classic songs that she carefully selected. 21 years since his first studio album, David Gray's tenth and latest, "Mutineers," finds the singer-songwriter steering into unfamiliar territory while cultivating a pugnacious, but respectful relationship with his own history.
WPOC Sunday in the Country
Sunday, September 24th, 2 p.m.
brGrab your cowboy boots and head over to Merriweather Post Pavilion for 93.1 WPOC’s Sunday in the Country! Artists featured include Rascal Flatts, Billy Currington, Scotty McCreery, Dylan Scott, Carly Pearce, and Levon. Crack a beer and enjoy an afternoon filled with great country music!
What’s Up? Spirit Festival
What’s Up? Media will host their first Spirits Festival at Annapolis Maritime Museum on Thursday, October 26th, 2017 from 6-9 p.m. Enjoy entertainment, live music by Bay Jazz Project, great food, cigar samples, raffle, and taste premium whiskey, scotch, malts, bourbon, rum, vodka, gin and much more. GET TICKETS >>
What's Up? Media Promotions
brWhat’s Up? Media loves our community and wants to give back. Check out our promotions page for opportunities to win amazing giveaways such as tickets to the most happening local events around, gift cards to your favorite local restaurants, and more! More details here.
brGrab your cowboy boots and head over to Merriweather Post Pavilion for 93.1 WPOC’s Sunday in the Country! Artists featured include Rascal Flatts, Billy Currington, Scotty McCreery, Dylan Scott, Carly Pearce, and Levon. Crack a beer and enjoy an afternoon filled with great country music!
What’s Up? Spirit Festival
What’s Up? Media will host their first Spirits Festival at Annapolis Maritime Museum on Thursday, October 26th, 2017 from 6-9 p.m. Enjoy entertainment, live music by Bay Jazz Project, great food, cigar samples, raffle, and taste premium whiskey, scotch, malts, bourbon, rum, vodka, gin and much more. GET TICKETS >>
What's Up? Media Promotions
brWhat’s Up? Media loves our community and wants to give back. Check out our promotions page for opportunities to win amazing giveaways such as tickets to the most happening local events around, gift cards to your favorite local restaurants, and more! More details here.
