Two boat shows that take up the whole harbor. Two Navy home games. The grand finale of the Renaissance Festival and all the fall fun you can handle. October in Annapolis has zero chill. Unless you’re talking about the kind that creeps in some mornings. That’s my favorite kind.
Anyhow . . . here’s everything circled on our calendar.
🎻 Annapolis Symphony opens its season – October 2–3
The Annapolis Symphony Orchestra launches its 2026–27 season, In Nature's Realm, with Signature Series I: Echoes of the Earth at 7:30 PM both nights at Maryland Hall. Cellist Julian Schwarz plays Jennifer Higdon's Cello Concerto. Tickets start at $25. One practical note for every Maryland Hall show this fall: the building is replacing its HVAC and installing new floor and ceiling tile, so parking, restrooms and the route to your seat can change show to show.
🏳️🌈 Annapolis Pride Parade & Festival – Saturday, October 3
The parade steps off from St. John's College and heads down West Street, then the festival takes over the Bates Athletic Complex. The whole thing runs 11 AM to 6 PM. This year's theme is "United in Pride, Together We Thrive!" and the parade grand marshal is singer-songwriter Ryan Cassata.
🎨 First Sunday Arts Festival – Sunday, October 4
As always on the first Sunday of the month, the Inner West Street Association closes the first block of West Street and Calvert Street from 11 AM to 5 PM for 150+ vendors, live music on multiple stages, and food trucks to complement West Street’s restaurants. Fair warning: October is the penultimate (AKA second to last) one of the year. December brings something new entirely. Hint: 🍫
🚲 Lifeline 100 – Sunday, October 4
Photo: Lifeline 100
The county's big community bike ride returns for a 12th year, starting and finishing at Kinder Farm Park in Millersville. There are 100-, 65-, 30-, and 15-mile rides, so there’s really something for everyone. The long routes tour county roads and feature some epic water views. The short ones stay on flat paved trails.
Late registration is $75 for the century and the 65, $55 for the 30 and the 15, and the field's capped at 1,000 riders. There’s also a Children's Bike Rodeo for ages 4 to 10 and a 2.6-mile Family Fun Safari Ride. Both free.
Every dollar goes to county nonprofits – the ride has raised more than $450,000 since it started!
🚤 Annapolis Powerboat Show – October 8–11
If you had to pick one city-defining event for Annapolis, it’d probably be a toss-up between boat shows and Blue Angels. And honestly, I’m gonna give it to the boat shows. It’s hard to overstate how important they are for the town (and local maritime businesses) economically. And it’s hard to overstate how darn cool they are. Case in point: they literally build a temporary floating marina in the harbor for the shows.
You don’t have to be rich. You don’t have to be buying a boat. Heck, you don’t even need to be a boater to enjoy the show. We can’t recommend it enough.
Photo: Kevin Snyder for the Naval Academy Athletic Association
Navy comes home for two games in October after a three-game road stretch: Tulsa on October 10 and North Texas for Homecoming on October 24. Both kick off at 3:30 PM, and if you can’t make it to Admiral Heights, you can watch on CBS Sports Network.
Navy football games are some of the best family-friendly fun to be had in Annapolis. First time? Check out our gameday guide!
⛵ United States Sailboat Show – October 15–18
At its core, Annapolis will always be a sailing town. In fact, the Annapolis Sailboat Show was the world’s first in-water sailboat show, and it’s still the largest. Just minutes after the powerboat show is closed, the motor yachts and center consoles start rolling out. Not long after that, hundreds of sailboats will pack the recently vacated temporary marina ready for a whole new crowd.
Just like the powerboat show, even if you aren’t a sailor, it’s hard not to have a good time. It’s also a great place to plan your next vacation because lots of charter companies from the Caribbean journey north to be part of it, and you don’t have to have Below Deck money to charter one.
And when the show closes Saturday: boat shows are all about the afterparties. And the biggest one is Party in the ’Port at Eastport Yacht Club. Don’t worry. It’s open to the public. The Slip Hippies open the night and local favorite One Night Only closes it down. There’s a chili bar, a regular bar 🍻, and absolutely no stuffiness allowed.
👉 Tickets
🩰 La Sylphide – October 16–18
Ballet Theatre of Maryland stages its first-ever La Sylphide at Maryland Hall: Friday at 7:30 PM, Saturday at 7 PM, Sunday at 2 PM. August Bournonville built it in 1836 and it's one of the oldest ballets still performed – Scottish Highlands, a groom who abandons his own wedding to chase a woodland spirit, and a witch who offers to help. The company sells tickets only through its own site or box office, and there's a virtual option if you'd rather watch from the couch.
🐉 DragonFest – Saturday, October 17
Naptown Scoop photo
The Annapolis Dragon Boat Club takes over lower Fourth Street at Pier 4 Marina from noon to 4 PM. And it's free to walk in. Live music, food and drink, a silent auction, raffles, and a chance to ask a paddler what dragon boating actually involves. The club is a community for people affected by breast cancer first and a boat club second, and this is its Breast Cancer Awareness Month fundraiser.
🖼️ Art @ the Park – October 17 & 18
The 36th annual show fills Quiet Waters Park from 10 AM to 4 PM both days. The festival is free but park entry is $8 per vehicle (free for military and veterans with ID). Bring the kids through the Recycled Mask Challenge: pick up a wooden "tree cookie" at the big playground in early October, glue on bottle caps, egg cartons, and pinecones, then bring it back on festival weekend to hang along the Concert Trail. Leashed dogs are welcome.
🍂 Maryland Avenue Fall Festival – Sunday, October 18
One of the longest-running street festivals in the state closes the first two blocks of Maryland Avenue, State Circle to Cumberland Court, from 10 AM to 5 PM. Free, rain or shine. Last year's edition included a 2 PM Pup Parade down the Avenue. Here’s hoping for round two of that.
🎸 Porchfest Annapolis – Saturday, October 24
Photo: Porchfest Annapolis
This one’s simple. Bands play on front porches. You listen in yards and streets. Everything’s acoustic or lightly amplified so it’s good for little kids and dogs. Shows run from 11 AM (ish) to 3 PM (ish). Park at Knighton or Park Place and walk in. Rain date: Sunday, October 25.
🚶 Eastport Shuffle – Saturday, October 24
The first one ever. The Eastport Civic Association leads a 1.5-mile guided walk through Eastport's streets and stories from 1:30 to 4:30 PM, starting at George Washington Davis Memorial Park at 399 Chester Ave. It's $30, kids 10 and under are free, groups are capped at 10 people, and Davis' Pub, the sponsor, buys everyone a drink at the finish. Proceeds fund ECA's community grants. Rain date: November 7.
🏰 Last call for Renn Fest – through Sunday, October 25
Revel Grove's 50th season ends October 25, and every October weekend is Harvest Hollow, with the decorations up along Mary's Dale Way and spooky-season shows on the schedule. Tickets are $31 for adults, $27 for seniors 62 and up, and $17 for kids 7 to 15, plus tax and fees. Single-day tickets are sold online only, and Sunday, October 11 offers ASL interpretation.
👻 Station 7 Terror Trail – Fridays and Saturdays, October 2–31
The volunteer firefighters in Gambrills run a three-quarter-mile haunted walk through the woods, 7:30 to 10 PM. It's $30, or $10 more for a Fast Pass, and the Boo Loop (the not-scary version for kids under 8) is $10. Bring a non-perishable food donation and take $2 off, same as first responders, veterans, teachers and medical pros. New this year: everybody parks at the Davidsonville Park-and-Ride, 2701 Davidsonville Road, and rides a free shuttle in. Last shuttle back leaves at 9:45 PM.
🎃 Great Annapolis Pumpkins & the Scarecrow Stroll – all month
Annapolis' classic giant pumpkins, 600 to 1,500 pounds each, arrive downtown just after the first weekend of October. They get carved the Friday before Halloween and stay out through November 2. Please don’t climb the pumpkins. They don’t appreciate it.
🎃 The rest of Halloween week – October 23–31
Halloween is a Saturday this year and the run-up is packed. The Colonial Players open The Legend of Sleepy Hollow on October 23 and run it through November 8 at their theater on East Street. Annapolis Harbour Center hosts Haunted Harbour Day on the 24th from 10 AM to 12:30 PM with store-to-store trick-or-treating, a balloon artist, and a costume contest at 11:30. County Animal Services runs its Howl-O-Ween party the same morning from 10 AM to 1 PM in Millersville with a trick-or-treat trail and Candy with a Cop. The Naptown Philharmonic plays its Halloween Spooktacular on October 25 at 3 PM in Key Auditorium at St. John's College, with the Marcolivia Duo, emcee Michael Hughes, and a costume contest for all ages. Then Annapolis Opera performs The Pirates of Penzance at Maryland Hall on the 30th at 7:30 PM, with a repeat November 1.
🎤 Dinner Under the Stars goes Motown – Saturday, October 31
West Street keeps its tables in the street through the end of the month. October 7 and 14 are branded Dinner on Deck for the boat show crowds, with Island Breeze playing on the 7th and Spa Creek Jazz on the 14th. October 21 is the last regular Wednesday, and the season closes Saturday, October 31 with a free Motown concert from Spice and Motown Magic, 6 to 9 PM. Motown costumes are optional. Dining runs 5 to 9 PM and reservations are always a good idea.
SEE YOU OUT THERE
