This week started out with some good news for Main Street Annapolis business owners, and some not-so-good news for area bicyclists; the trial bike path that divided a city has been removed, at least for now. The decision to remove the bike path was made after two weeks of observation and the Mayor’s meeting with Main Street merchants, most of them expressing concern over the limited parking resulting from the bike path and its potential to lessen traffic to their businesses. 

In a statement, Buckley said,

What this experience also demonstrated to me is that we must prioritize the replacement of Hillman Garage, including additional parking, before we move forward with any projects on Main Street.

The investment we made in this trial was not just a one-time thing. We now own these materials. We will repurpose the tables and chairs, as well as the construction materials, over the next three years throughout the City with other proposed bike paths and pop-up projects. We hope to support other businesses areas like Maryland Avenue, West Annapolis, and Fourth Street in Eastport with these ideas and materials. 

The removal of the bike path comes just in time for one of the city’s biggest annual events, the United States Sailboat Show. Sailing into Annapolis for its 49th year, the world’s largest and most prestigious sailboat show will feature boats from all over the world in addition to vendors, workshops, prizes, cocktail and wine tastings and schooner sailing cruises. See the official event guide here


Navy Men’s Soccer vs. American University — Oct. 3, 7 – 9 p.m.

The Navy men’s soccer team plays American University. Come root for your favorite Annapolis team at the Glenn Warner Soccer Facility. Free admission. 

United States Sailboat Show — Oct. 4 – 8, 10 a.m. – 5 p.m.

In October sailors from around the globe will gather on miles of docks in beautiful downtown historic Annapolis for the 2018 United States Sailboat Show. This is an internationally acclaimed sailboat show, recognized as the world’s largest and most prestigious sailboat show.

Tickets are available online or at authorized ticket booths only.

Navy Women’s Volleyball vs. Colgate University — Oct. 5, 7 – 9 p.m.

The Navy women’s volleyball team plays Colgate University. Come root for your favorite Annapolis team at the Wesley Brown Field House. Free admission. 

Ghost Tours Annapolis: Historic Hauntings — Fridays and Saturdays, Oct. 5 – 27

During the Month of October- Includes the Spooky Interior of a historic home. Exclusively available after hours to Annapolis Tours by Watermark’s guides and guests. Step inside and discover a ghost story of your own!

Looking for ghost tours in Maryland? This year instead of heading to the usual Haunted House full of unconvincing tricks, come with Watermark on a special haunted ghost tour of Annapolis during the festive month of October. Special Historic Hauntings takes guests inside one of Annapolis’ most notoriously haunted houses! Step back into time and hear the tales of the spirits that linger inside the dimly lit mansion. Only our ghoulish guides have access to bring you inside this haunted structure after dark. No visit to Annapolis is complete without seeking out the spirits!

Lifeline 100 Bike Ride — Oct. 7, 7 a.m.

The annual Lifeline100 at begins at Kinder Farm Park in Millersville, MD  and offers a unique organized ride experience for cyclists of all ages and abilities with scenic 100 and 65 mile routes on road and paved trail and 30 and 15 mile routes on paved trail only. Younger children can learn bike safety at the free children’s Bike Rodeo provided by Anne Arundel County Police Bike Patrol.   Thanks to our generous sponsor Prophasys, riders with special needs and their accompanying rider can register at a special 2 for 1 rate.

Who’s at Rams Head? 

Tuesday, 10/2: Basia

Wednesday, 10/3: Rockapella

Thursday, 10/4: The English Beat

Friday, 10/5: Michael Franks

Saturday, 10/6: Martin Barre of Jethro Tull

Sunday, 10/7: A Special Acoustic Solo Performance with Anders Osborne *Matinee Show*

                          The Manhattan Transfer

More information and details about these shows can be found here

Recurring Events

Maryland Renaissance Festival — Weekends until Oct. 21, 10 a.m. – 7 p.m.

The Maryland Renaissance Festival is back for its 41st season! The festival includes 200+ entertainers, ten stages, a 3,000 seat jousting arena, 122 craft shops, 48 food and beverage emporiums, games, attractions and 85 acres of complimentary parking. Hang out with King Henry and his court in the 16th-century English village, Revel Grove and let merriment abound. 

Greenstreet Gardens Fall Festival — Oct. 6 and 7, 10:30 a.m. – 5 p.m.

Hay Rides • Jumping Pillow • Tire Tower • Corn Maze • Underground Slide • Corn Box, and Much, Much More!

Homestead Gardens’ 35th Annual Fall Festival — Oct. 6 and 7, 11 a.m. – 5 p.m.

Celebrate Autumn at Homestead Gardens’ 35th Annual Fall Festival – the largest in the area!

With a wide array of attractions and entertainment for kids of all ages, your experience is sure to be an unforgettable one.
From our store, to the barnyard, through the corn maze and pumpkin patch, Homestead Gardens is alive with the colors of fall.

First Sunday Arts Festival — Oct. 7, 11 a.m. – 5 p.m.

The Arts Festival is held every Sunday from May 6th to November 4th on West Street in Downtown Annapolis. Shop from 130 local and regional artisans and enjoy outdoor cafes and more than seven live bands each day.  You can even explore galleries, take a game room challenge and even create your own artwork at shops on West Street. 

Sunday Outdoor Free Movies in the Garden — Oct. 7, 8:30 – 10:30 p.m.

First of all, who doesn’t love a Free Movie Screening? Add the fact that it is outside under the beautiful Annapolis sky, and you automatically have a family friendly, romantic, relaxed Sunday evening!

Every Sunday Night our Beer Garden becomes your Neighborhood Outdoor Movie Theatre with Free Classic Movie Screenings. All screenings are free and open to the public. Because all of our screenings begin at dusk, the start time may vary throughout the season.