October in Maryland is hard to beat.
Cooler mornings, changing leaves, pumpkin everything, football weekends and a calendar packed with festivals make this one of our favorite times of year to get out and explore.
Whether you're looking for something to do with the kids, a fall date night, a festival with friends or just an excuse to spend the day outside, we've rounded up some of the best events happening this October around Annapolis, Severna Park, Baltimore and Baltimore County.
Save a few dates and enjoy fall in Maryland!
⚓ Annapolis Powerboat Show
October 8–11 | Downtown Annapolis
One of Annapolis' signature events returns to City Dock this October.
The Annapolis Powerboat Show transforms the downtown waterfront with boats, marine gear, demonstrations and exhibitors from around the boating world.
Even if you're not currently shopping for a boat, it's a great excuse to spend a fall day downtown, grab lunch and enjoy Annapolis when the waterfront is buzzing.
⛵ Annapolis Sailboat Show
October 15–18 | Downtown Annapolis
The following weekend, it's the sailors' turn.
The Annapolis Sailboat Show fills the harbor with sailboats from around the world and brings thousands of sailing enthusiasts into downtown Annapolis.
Walk the docks, explore the boats and then stick around for dinner downtown. It's quintessential Annapolis in the fall.
🎃 Find the Great Annapolis Pumpkins
Beginning October 10 | Downtown Annapolis
Keep an eye out for some VERY large pumpkins popping up around downtown Annapolis this month.
The Great Annapolis Pumpkins return October 10, with enormous real pumpkins — some weighing more than 1,000 pounds — displayed around town.
They're free to visit and make a fun excuse to wander downtown, grab a coffee and get a few fall photos.
The pumpkins will be carved on October 29, just in time for Halloween.
🎨 Maryland Avenue Fall Festival
October 18 | 10 AM–6 PM | Downtown Annapolis
Spend a Sunday strolling one of Annapolis' prettiest streets during the Maryland Avenue Fall Festival.
Maryland Avenue from State Circle to Cumberland Court becomes part of the celebration, making this a fun way to experience the Historic District during one of the nicest months of the year.
Make a day of it and walk over to Main Street or City Dock afterward.
🎃 Pumpkins & Crafts at Kinder Farm Park
October 11 | 11 AM–2 PM | Millersville
For families around Severna Park, Kinder Farm Park is always worth having on your fall list.
On October 11, head to the Black Oak Pavilion for pumpkin painting and fall crafts.
And if you haven't explored Kinder Farm Park before, give yourself some extra time. Between the walking trails, farm animals and historic farm setting, it's a great place for an easy fall afternoon with kids.
🌾 Make Your Own Scarecrow at Kinder Farm Park
October 17 | Noon–3 PM | Millersville
Kinder Farm Park is back on our list the following weekend for one of those activities that just feels like October.
Families can build their own scarecrow at the Black Oak Pavilion and then explore the Historic Farmhouse Museum and sawmill.
Definitely one for the kids.
Honey Harvest Festival at Oregon Ridge
October 4 | Oregon Ridge Nature Center, Cockeysville
Here's a fun one if you're looking to head north of Baltimore.
Oregon Ridge Nature Center's Honey Harvest Festival celebrates one of nature's hardest-working little creatures.
Visitors can learn about beekeeping, taste local honey and enjoy family-friendly activities centered around bees, pollinators and sustainability.
Bonus: Oregon Ridge is especially beautiful once the fall colors start arriving, so leave time for a walk.
Roktoberfest at Guinness
October 9–11 | Guinness Open Gate Brewery, Halethorpe
October without Oktoberfest? Not happening.
Guinness Baltimore keeps the celebration going with Roktoberfest, featuring live rock music under its Munich-inspired tent, Oktoberfest beers and Bavarian-inspired food.
This one's an easy pick for a fall afternoon or night out with friends.
Das Best OktoberFest
October 10 | Maryland State Fairgrounds, Timonium
If you're ready to fully commit to Oktoberfest, head to the Maryland State Fairgrounds.
Das Best OktoberFest brings craft beer sampling, German food, live entertainment, oompah music and even a little tug-of-war to Timonium.
Grab some friends, break out the lederhosen if you're feeling ambitious, and make an afternoon of it.
Parkville-Carney Festival
October 10 | Parkville
Food trucks, craft vendors, live entertainment and a car show all come together for this community festival in Parkville.
It's an easy local option for families who want some fall festival fun without making an entire weekend trip out of it.
Makers Valley Fall Festival at Boordy Vineyards
October 17 | Hydes
Wine + fall in the Maryland countryside is a pretty good combination.
Boordy Vineyards hosts the Makers Valley Fall Festival with live music, more than 35 vendors, food trucks and, of course, Maryland wine.
This would be one of our picks for an October date day or an afternoon out with friends.
Hereford Fall Festival
October 17–18 | Parkton
Head north into Baltimore County for a true community fall weekend.
The Hereford Fall Festival returns to Parkton October 17–18 and is a great excuse to take a drive through northern Baltimore County just as the leaves are beginning to show off.
Maryland Fall Home & Garden + Craft Show
October 16–18 | Maryland State Fairgrounds, Timonium
We might be a little biased, but obviously this one belongs on the list.
More than 300 exhibitors are expected at this year's Maryland Fall Home & Garden + Craft Show, including over 100 local crafters.
You'll find home improvement ideas, landscaping and outdoor-living inspiration, shopping, kids' activities, a petting zoo and plenty of ideas to take home for your own space.
For anyone thinking about renovating, decorating or tackling that next house project, this is a good one.
ZooBOO! at the Maryland Zoo
Select weekends throughout October | Baltimore
Halloween takes over the Maryland Zoo throughout October with ZooBOO!
This year's festivities include trick-or-treating throughout the Zoo, an inflatable corn maze, pumpkin patch, crafts, costume contests, food trucks, animal ambassador encounters, games and special performances.
ZooBOO! runs October 2–4, 9–11, 23–25 and 30–31 and is included with regular Zoo admission or membership.
Costumes encouraged, obviously.
OktoBEARfest at the Maryland Zoo
October 16–17 | Baltimore
The kids aren't the only ones getting an October event at the Zoo.
OktoBEARfest returns October 16–17 with fall beer, seasonal festivities and animal experiences. The weekend includes a Friday-night 21+ celebration along with additional festivities Saturday.
Definitely one of the more unusual Oktoberfest settings you'll find around Baltimore.
Art @ the Park
October 17–18 | Quiet Waters Park, Annapolis
If your ideal fall weekend involves art, trees and a beautiful park rather than pumpkins and beer, put this one on your calendar.
Art @ the Park brings artists and makers to Quiet Waters Park in Annapolis for a weekend surrounded by one of Anne Arundel County's prettiest outdoor settings.
October is also a wonderful time to explore the park itself.
Get Out and Enjoy Maryland
One of the best things about living in this part of Maryland is how much there is to do within a relatively short drive.
You can spend Saturday morning at a farm in Anne Arundel County, Saturday evening on the Annapolis waterfront and Sunday hiking through Baltimore County — and still be home in time for the Ravens game.
October goes quickly, so pick a few things from the list, grab your favorite people and enjoy it while it's here.
And if exploring a new neighborhood this fall has you wondering what it might be like to live there, that's where we come in.
Keith Walsh Home Team
Helping you find home throughout Maryland. 🏡
