☕ The Great Annapolis Pumpkin Spice Coffee Crawl – 9/27–11/3

Lovingly called TGAPSCC2023 for "short". Everything you need to know is at annapolis.coffee (coolest domain ever, right?) but here's the skinny pumpkin spice latte: drink local coffee, fill out the TGAPSCC2023 punch card, get a treat.

UPDATE: Only the first 25 punch cards get a free Drink Local or Die Trying shirt but any punch cards completed after get 25% in the TGAPSCC2023 shop.

‍

🧛🏻‍♂️HERE. a Pop-up Shop – 10/20–11/12

El Lunay's local pop-up shop features nearly a hundred local artists several times a year around town. This is her longest pop-up yet! It's also the only place to get Naptown Scoop's official gear (like hats, shirts, and limited edition Smith & Quinn quarter zips.

Check here for hours. 4 Church Circle, Annapolis, MD 21401.

🧙🏻Halloween Costume Exchange – 10/7 & 10/14

Macaroni Kid’s solution to those costumes your kids outgrew after just one year. Show up with gently worn costumes and accessories and swap for new ones. 10/7 & 10/14 outside of Wimsey Cove framing.

10:30 AM–1:30 PM @ Parking lot in front of Wimsey Cove Framing & Fine Art Printing, 209 Chinquapin Round Road, Annapolis, MD 21401. Learn more.

🎃 Great Annapolis Pumpkins – 10/9–31

Downtown Annapolis Partnership (DAP) hides several of them around Annapolis every fall. Since these gorgeous gourds are funded by sponsors and bought at auction, you never know how many we’re gonna get. This year, DAP snagged 10 pumpkins – 5 of which were over 1,000 pounds and only 1 of which fell off the truck on the way home. Oops.

Different locations in Annapolis. Click here.

View this post on Instagram

A post shared by Maddie | DMV Food, Fitness, & Fun (@dmvfoodfinds)

🕯️ Special Historic Hauntings – 10/12

Watermark teams up with Historic Annapolis every Thursday, Friday, and Saturday in October for a walking tour of Annapolis’ lesser-known haunted sites.

7:30–9:10 PM @ 188 Main Street, Annapolis MD 21401. Tickets.

👹 Very Superstitious: Friday the 13th at the Paca House – 10/13 (UPDATE: Sold out)

Join a candlelit tour of the William Paca House & Garden. 10/13, ages 10+.

5*–6 PM @ William Paca House & Garden, 186 Prince George St, Annapolis, MD 21401. Tickets.*

🍂 ATC Fall Fest – 10/15

Pick your own pumpkin, make s’mores, explore a hay maze, and more. The first 600 kids get a free gift if you donate canned goods to the Food Bank.

12–3 PM @ Annapolis Town Center, 1906 Towne Centre Boulevard Annapolis, MD 21401. Free but registration is required.

🪦 St. Anne’s Cemetery Tour – 10/14

Take a tour of the historic cemetery at Hammond-Harwood house.

11 AM–12 PM @ St. Anne's Cemetery, Annapolis, MD 21401. Tickets.

🕯️ Spirits of the Past Tour – 10/16–31

Embark on a chilling journey through the haunted history of the William Paca House this October! Guided by candlelight, dive into tales of past illnesses, spine-tingling treatments, and mourning rituals. Limited space—register in advance for an eerie escapade!

11 AM–3:30 PM @ William Paca House & Garden, 186 Prince George Street. Tickets

🎥 Retro Replay – 10/17

Landmark Theatres at Annapolis Harbour Center is rolling out '80s horror films every Tuesday in October and switching it up with some Tom Hanks classics in November.

1:30–7:30 PM @ Annapolis Harbour Center, 2512 A Solomons Island Road, Annapolis, MD 21401. Get tickets.

🎤 Thriller Karaoke Night – 10/20

Get ready for a night of frightful fun at Marlyland Hall’s Thriller Karaoke – (Costume) Night! Show your confidence with spooky tunes, imaginative costumes and themed drinks. The event includes a Costume Contest, a Raffle Extravaganza with pumpkin prizes, and a bowl of Halloween treats!

6–8 PM @ Maryland Hall, 801 Chase Street, Annapolis, MD 21401. Learn more.

🧑🏻‍🌾 Scarecrow Stroll – 10/20-11/1

The lamp posts encircling West Street will be decorated with themed scarecrows. The deadline to join the contest has closed.

@ West Street, Annapolis, MD 21401. Learn more

👻 Haunted Harbour Day – 10/21

Annapolis Harbour Center throws a haunted fest with trick-or-treating, costume contests, raffles, and more.

10 AM–12:30 PM @ Annapolis Harbour Center, 2512 A Solomons Island Road, Annapolis, MD 21401. Learn more

🎆 Fall Fest on West – 10/21

Live music, pumpkins, and kids' fun on West Street, Historic Annapolis followed by Dinner Under the Stars with live music.

2–9 PM @ West Street, Annapolis, MD 21401. Learn more

🍻 Shoptoberfest – 10/21

It's a local shop extravaganza with a blend of Halloween and Oktoberfest flair. And here's the best part – exhibitors can showcase and sell their awesome products/services right from their booths.

11 AM–3 PM @ Severna Park Racquetball & Fitness Club, 8514 Veterans Highway Millersville, MD 21108. Learn more.

🎪 Maryland Avenue Fall Festival – 10/22

Join the Annapolis Tradition for a free street fest filled with arts, crafts, antiques, and live music on historic Maryland Avenue! Dive into the charm of one of the oldest commercial streets in the U.S., featuring hidden gardens, vintage vinyls, and more.

10 AM–5 PM @ Maryland Avenue, Annapolis, MD 21401. Learn more.

🚲 Halloween Bike Party – 10/26

Get ready to pedal into the Halloween spirit. It’s a fun ride lasting 60 minutes and costumes are recommended. Whether on two wheels or electric scooters, all are welcome to join

7 PM @ Meet at Acton Cove,14 South St, Annapolis, MD 21401. Learn More.

⚓ Annual USNA Halloween Concerts – 10/27

Led by Chapel Organist Monte Maxwell, this event features midshipmen's talents, a mashup of musical genres, and special effects. It's a spooky celebration of good conquering evil on All Saints' Day! A USNA shuttle will be running for all performances.

7–10 PM @ USNA Chapel, 121 Blake Rd, Annapolis, MD 21401. Tickets

🎃 Pumpkin Walk – 10/27

Hammond-Harwood House hosts a family-friendly costume parade around the mansion. Adult beverages for you, snacks for the kids. It’s a win-win.

4–6 PM @ Hammond-Harwood House, 9 Maryland Avenue. Annapolis, MD 21401. Tickets

🌃 Night Market – 10/27

The ground floor of the new Hillman Garage has morphed into a night market. Fusion of farmers' delights, vintage treasures, and artistry.

4–9 PM @ Noah Hillman Garage, 110 East St, Annapolis, MD 21401. More Details

🛶 Annual Halloween Paddle – 10/28

Throw on your best costume and paddle down Spa Creek with Capital SUP.

9:30–11 AM PM @ Meet at City Dock, Dock St, Annapolis, MD 21401. Tickets

💀 Day of the Dead Festival – 10/28

Get ready for a ghostly good time with a kid's zone, vibrant vendors, sugar skull face painting, traditional dance, and a DJ. Dress up, celebrate, and join the Halloween fiesta – it's a free, lively event supporting community diversity and cultural joy.

3–8 PM @ Maryland Hall, 801 Chase Street, Annapolis, MD 21401. Learn more.*

🪶 Whispers of the Raven – 10/28

Step into Hammond-Harwood’s ballroom for an Edgar Allan Poe-inspired evening of music and readings.

7–8 PM @ Hammond-Harwood House, 9 Maryland Avenue. Annapolis, MD 21401. Tickets

💐 Wildberry Halloween Field Market – 10/28

Come dressed up and trick-or-treat throughout the market.

9–1 PM @ Crownsville, MD 21032. Stay tuned for the vendor lineup.

👟 SPCA Haunted Trails – 10/28-29

Each day the dog walking trails will transform into the family-friendly "Trick or Treat Trail" by day and frighteningly live "Forest of Fear" at night. All proceeds benefit the SPCA of Anne Arundel County.

12–5 PM @ SPCA, 1815 Bay Ridge Avenue, Annapolis, MD 21401. Trick or Treat Trail

7:30–10 PM @ SPCA, 1815 Bay Ridge Avenue, Annapolis, MD 21401. Forest of Fear Haunted Trail

🧟 Zombie Dash 5K – 10/29

The Brick Companies host a costume run at the Smithsonian Environmental Research Center. Proceeds benefit the center.

*10 AM @ Smithsonian Environmental Research Center (SERC), 647 Contees Wharf Rd, Edgewater, MD 21037. ***Tickets

🌕 Full Moon Tour – 10/29

Join the Full Moon Tour at Hammond-Harwood House, where history unfolds under the moonlit sky. Discover the lock-down rituals of the Loockerman family. After the tour, relish the atmosphere with mulled cider on the patio.