Observe the biggest Tug of War over a body of water between decades'-old rivals, the residents of Eastport and the residents of Annapolis. Known as "Slaughter across the Water", it's become a beloved annual charitable event with a party on each side afterwards. Spectators can view the spectacle from City Dock on the Annapolis side or, on the Eastport side, Second Street near the Chart House Restaurant. For a spectacle of a different sort, pack the kids in the car and head to Sandy Point State Park any night beginning mid-November for Lights on the Bay, a spectacular drive-through holiday lights show beside the Chesapeake Bay featuring more than 60 animated and stationary displays. Another beautiful display happens just two evenings in November, Annapolis by Candlelight. During this walking tour in historic Annapolis, participants glimpse the interior of some of the city's most impressive historic private homes. 

Tree Lighting at City Dock

Dia De Los Muertos (The Day of the Dead) 

When: Saturday, November 2nd, 2019; 5:00 p.m. to 12:00 a.m.
Where: Annapolis Design District (Edgewood Ave. & Margaret Ave.)
Admission: Free

Celebrate and learn more about the Hispanic community of Annapolis during the Dia de Los Muerots block party. The event is free for all ages and a great way for family and friends to come together as a city and celebrate the Annapolis Hispanic community. The event features delicious food, beer & wine sales, Mariachi music, local artisans, a kids zone, costume contest, salsa dancing and lessons, and more.

Maritime Republic of Eastport's Tug o' War X
When: Saturday, November 2nd, 2019; 12:00 p.m.
Where: Eastport & Annapolis City Dock
Admission: Free

Drawing on a decades-old rivalry, the annual charitable event features the longest tug-of-war over a body of water in the world, pitting downtown Annapolitans against the rebels of the mock-breakaway Maritime Republic of Eastport. Dubbed the Slaughter across the Water, it features a 1700-foot rope, 450 tuggers and 1000 spectators. A festival-like atmosphere overtakes downtown Eastport and Annapolis beginning at 11:00 a.m. Tugging begins promptly (more or less) at the crack o' noon. Eastport vs Annapolis Tug of War

Annual Annapolis by Candlelight
When: Friday-Saturday, November 8th-9th, 2019; 5:00 p.m. to 9:00 p.m.
Where: Historic Annapolis - 42 East Street
Admission: $35-$50 per person

Let Historic Annapolis introduce you to some of the city’s finest architecture in its annual walking tour of private homes. This year’s tour focuses on historic neighborhoods in the vicinity of Prince George and King George Streets. Highlights include the Bordley-Randall House, a grand five-part colonial mansion; the Charles Carroll the Barrister House, an 18th-century building that Historic Annapolis moved in 1955 to save it from demolition; and the Patrick Creagh House, one of the best surviving examples of a home built for a member of the colonial merchant class. 

Annapolis by Candlelight

First Sunday Arts Festival

When: Sunday, November 3rd, 2019; 11:00 a.m. to 5:00 p.m.
Where: West and Calvert Streets
Admission: Free

Enjoy live entertainment as you stroll along the Annapolis Arts District on West Street and discover the work of 100 local and regional artists in search of unique holiday gifts. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. 

Lights on the Bay
When: November, 23rd, 2019 to January 1st, 2020; 5:00 p.m. to 10:00 p.m. nightly, weather permitting
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: $15 car; $50 bus

Don't miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit the Annapolis-based SPCA. 

Lights on the Bay

Grand Illumination – City Tree Lighting 

When: TBD
Where: Market Space at the Market House, 25 Market Street, Annapolis

With support from the Annapolis business community, the Annapolis Jaycees (Junior Chamber of Commerce) will once again host the Lighting of the Tree in Annapolis during the city’s Grand Illumination event. Watch Santa arrive in town and enjoy singing and dance performances by area youth. The Jaycees will provide refreshments and ornaments children can use to decorate the tree. Attendees are invited to bring nonperishable food items and new, unwrapped toys for the Jaycees’ annual Angel Tree Project.  

Thinking of a overnight stay? Discover local lodging in Annapolis and additional lodging options located just 25 minutes north at TheHotelsAtBWI.com.