Happy Halloween! All the events I’ve been posting about for the last month (or more?) have been slowly but surely leading up to the spookiest night of the year. (And the day of the year that Americans will spend the most money for, after Christmas, with this year’s spending expected to reach $9 billion — can you even imagine? That’s a lot of candy.) 

The festivities don’t end after Wednesday night though, especially if you live in Eastport. The annual Maritime Republic of Eastport’s Tug Of War is scheduled for this Saturday, which happens to be the day after your Annapolis.com editor (that’s me, hello!) moves into her new Eastport apartment. She will definitely be there taking photos and embracing all the quirkiness of her new neighborhood. 

#ThisWeekinAnnapolis

Annapolis by Candlelight — Nov. 2 and 3, 5 – 9 p.m.

A crisp autumn evening is the perfect time to walk through one of the historic neighborhoods of Annapolis.  The experience is even better when the doors to some of the homes are open and you are invited inside.  Each year in early November, Historic Annapolis showcases privately-owned historic houses on its popular Annapolis by Candlelight tour.  Visitors see how 21st-century Annapolitans care for and live in buildings constructed in the 20th, 19th, and 18thcentury.  Each house is a reminder of the rich architectural and cultural heritage of Maryland’s capital city and illustrates the practical and aesthetic benefits of effective historic preservation.

Dia De Los Muertos block party — Nov. 2, 5 – 11 p.m.

The City of Annapolis, The Center of Help and The Design District invite you to a Dia De Los Muertos block party! Free for all ages, featuring beer and wine, Latin food, mariachi music, salsa dancing & classes, an art and handcrafts gallery, costume contest and kids zone. Meet internationally-renowned artist Jesse Raudales. Dress as a Mexican skeleton! 

1st Annual Senior Stroll — Nov. 3, 10 a.m. – 12 p.m.

The first annual “Senior Stroll” for this 501(c)3 non-profit that rehabs and rehomes senior dogs. Registration includes a t-shirt. Bring your friendly (leashed) pup with you, or just come and meet some of our sugar-faced super seniors who are searching for their forever home. Browse local vendors, watch K9 demos, enjoy a dog costume contest, and get some delicious food. Registration starts at 9 and the walk starts at 10. $25 per person. 

Maritime Republic of Eastport Tug Of War — Nov. 3, 10:30 a.m. – 6 p.m.

Billed as the longest International** Tug of War over water in the world, The Tug of War was originally conceived by the residents of Eastport in 1997 when the City of Annapolis used the excuse of a “public works project” to close the Spa Creek bridge that leads to Eastport from Annapolis. This unprovoked act of aggression on the part of the City of Annapolis had the effect of cutting off Eastport residents and businesses from the rest of the city. The somewhat fractious citizens of Eastport, feeling the sting of rejection by The City and, perhaps, somewhat emboldened by the generous pouring habits of a local bartender, decided to declare war against The City of Annapolis and secede. Thus, to the rallying cries of “Up The Republic,” the micro-nation known as The Maritime Republic of Eastport was born.

Across the Bay 10k — Nov. 4, 6 a.m. – 12 p.m.

The Across the Bay 10k is one of the largest, most exciting mid-distance events anywhere. 4.35 miles of the 10k course takes place over water on the Chesapeake Bay Bridge near Annapolis, Maryland. The event lasts all weekend and will include a 10k, kid’s fun run during the race expo at Navy-Marine Corps Memorial Stadium, and a live concert on race morning at the finish line in Queen Anne’s County that is free and open to all.

Recurring Events

James Brice Hard Hat Tour — Nov. 24, 10:30 a.m. – 12 p.m.

Have you ever wondered what preservation in progress really looks like?  Take a peek behind the scaffolding at the James Brice House, where a major preservation effort is underway to restore the house to its 18th century grandeur.  Join one of our public tours to peer beyond the sawdust and learn about the people who built the house, lived and worked in it, and the craftsmen restoring it today.

First Sunday Arts Festival — Nov. 4, 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.