Halloween falls on a Saturday this year, and downtown Annapolis has spread its events out across the day, from an 11 a.m. house tour to a Motown set that ends at 9 p.m. Until late afternoon, the events come one after another, so you can do them in order. In the evening they overlap, and you'll have to pick.
Here is the day as it has been announced:
- 11 a.m. to noon: "Very Superstitious!" guided tour of the William Paca House and Garden, from Historic Annapolis
- 3 to 8 p.m.: Day of the Dead Festival on the front lawn of Maryland Hall, 801 Chase Street, free
- 5 p.m.: Outdoor dining opens on the first block of West Street
- 6 to 9 p.m.: Spice and Motown Magic play a free concert on that same block
- 8 p.m.: The Colonial Players stage The Legend of Sleepy Hollow
Why Saturday Is Open
Two things that often fill a fall Saturday in Annapolis aren't happening in town this time.
The first is Navy football. According to the Navy football 2026 schedule, the Mids play Notre Dame at noon on October 31 in Foxborough, Massachusetts. That's an away game, so no home crowd will be heading to the stadium that afternoon.
The second is the opera. Annapolis Opera has The Pirates of Penzance at Maryland Hall at 7:30 p.m. on Friday, October 30, and 3 p.m. on Sunday, November 1. There's no Saturday performance. Maryland Hall's own events calendar shows the free Day of the Dead Festival on Saturday, between the two opera dates.
Halloween itself is in the middle of a busy weekend. The Colonial Players also perform The Legend of Sleepy Hollow at 8 p.m. Friday and 2 p.m. Sunday. Saturday is the one day of the weekend when the big indoor and outdoor events are spread out across the hours.
Late Morning: Superstitions at the Paca House
The day opens with history. Historic Annapolis runs its "Very Superstitious! Paca House and Garden Tour: A History of Luck, Lore, and Beliefs" from 11 a.m. to noon on October 31. It's a guided walk through the William Paca House and Garden that covers household rituals, good-luck charms and protective practices from earlier centuries, some of which people still follow today. After the tour, guests are invited to stay for seasonal refreshments and share a favorite superstition.
Tickets are $15 for general admission and $12 for Historic Annapolis members and military. Historic Annapolis recommends registering in advance because space is limited. The tour goes inside the house, which means climbing and descending several flights of stairs, and weather or private events can change the route.
The tour ends at noon, and the next event starts at 3. That leaves time for lunch at home or downtown before the afternoon starts.
Afternoon: Altars on the Maryland Hall Lawn
At 3 p.m. the day moves to Maryland Hall. The Day of the Dead Festival, or Día de los Muertos, is listed as "City of Annapolis Presents." It takes place on the Front Lawn and is free to attend. Eye On Annapolis reports that it runs from 3 to 8 p.m., with live music, traditional dancing, cultural displays, art, food, children's activities and altars honoring family members and friends who have died.
The timing is a little ahead of the holiday. The same Eye On Annapolis piece notes that Día de los Muertos is traditionally celebrated on November 1 and 2, when families build altars, set out photographs and share memories. Holding the Annapolis festival on Halloween puts it right before those days, on a Saturday afternoon when families can attend.
Five hours is a long window. You don't have to arrive at 3 to see it. That matters, because the evening schedule overlaps the festival's last three hours.
Five O'Clock Is When the Day Forks
Until 5 p.m., you can go to one thing after another without missing anything. After that the events overlap. Three of them claim the same evening hours:
- Maryland Hall's Front Lawn keeps the Day of the Dead Festival going until 8 p.m.
- The first block of West Street opens for outdoor dining at 5 p.m., and the free Motown concert runs from 6 to 9 p.m.
- The Colonial Players start The Legend of Sleepy Hollow at 8 p.m.
There are a few ways to put the evening together. If you have kids, you could stay at the festival until dark and then head over to West Street for the second half of the concert. If you want dinner and music, a West Street table at 5 gets you a seat before the band starts at 6. If you have theater tickets, you can listen to an hour or more of Motown before an 8 p.m. curtain. The Colonial Players sell tickets online for all three weekend performances, so if Saturday doesn't work, you can still see the show on Friday or Sunday.
Dinner Under the Stars Was Supposed to Be Done
In September we wrote that West Street's Dinner Under the Stars ended September 30. That was the end of the Wednesday-night season, and it wasn't the last of the series. Eye On Annapolis reported in late September that the September 30 night would have a DJ and the season's last line-dancing lessons. The series then came back as "Dinner on Deck" during the Annapolis Boat Shows on Wednesday, October 7, and Wednesday, October 14.
Halloween is the series' second encore, and this one falls on a Saturday instead of a Wednesday. The Inner West Street Association's event page describes it this way:
"Enjoy timeless hits, great music, and a fun atmosphere for the whole family. Bring your lawn chairs, blankets, and friends for a night of unforgettable entertainment. Motown costumes optional!"
The association's page lists the concert from 6 to 9 p.m., with outdoor dining starting at 5. The Eye On Annapolis announcement gives 5 to 9 p.m. for the whole evening. Both are correct. Dinner comes first, and the band comes on an hour later.
Up West Street, 49 West Has a New Owner
This is the first Halloween at 49 West Coffeehouse, Winebar & Gallery under its new owner. Eye On Annapolis reported in August that Myriam Osorio McCormick, owner of McCormick Bakery & Chocolate Factory, bought the West Street restaurant and music venue from Brian and Sarah Cahalan, effective September 1, 2026.
According to that report, the plan keeps the parts regulars know. The live music room, which is known for jazz, folk and singer-songwriters, is expected to keep operating, and the current staff is expected to stay. The biggest planned addition is a sweets counter with McCormick chocolates, pastries and desserts, along with some renovations and updates. Those were plans as of late August. If the sweets counter is the reason you'd stop by, look before you go.
The 49 West calendar shows a $15 listing on October 31. If you're planning around the music room, check that page for the performer and set time.
The First Block Comes Back on November 14
The first block of West Street near Church Circle, where the Motown concert happens, has one more event this fall. Tastings & Tunes: Wine & Beer Fest on West is set for Saturday, November 14, from 1 to 4 p.m. It's a ticketed event with wine, beer and live music, and it wraps up West Street's fall schedule. Tickets are sold through Naptown Tickets.
Before that, there's Saturday's Halloween lineup. Most of the day lets you go from one event to the next. After 5 p.m. you'll be choosing between the festival lawn, the West Street concert and the 8 p.m. curtain, and the Halloween concert on West Street ends at 9.
Brian Jacobs works from Coldwell Banker Realty's Church Circle office, and he follows how downtown's calendar shapes life on each street. If you're thinking about a home within walking distance of nights like this one, Annapolis Fine Property is glad to walk through it with you. Get a positive, helpful partner and schedule a consultation.
