Annapolis Fall Guide 2026: Events, Date Ideas, Pumpkin Patches & Things to Do
Looking for the best things to do in Annapolis this fall? Fall 2026 brings Navy football, waterfront concerts, the Annapolis Songwriters Festival, the Maryland Renaissance Festival, pumpkin patches, local food and some of the best weather of the year for exploring Annapolis.
Whether you live here, are visiting for the weekend, or are thinking about moving to the Annapolis area, this guide covers some of our favorite ways to experience fall in and around Annapolis.
What are the best things to do in Annapolis in fall 2026?
If you only have a weekend, start with Downtown Annapolis and the waterfront, then build your plans around one of the area’s major fall events.
Here are some highlights:
Fall Activity | When/Where |
September Sunsets Concert Series | Thursdays, Sept. 3–24, Annapolis Maritime Museum Park Campus |
Navy vs. Towson | Sept. 5, Navy-Marine Corps Memorial Stadium |
Annapolis Songwriters Festival | Sept. 10–13, Downtown Annapolis |
Boatyard Beach Bash | Sept. 19, Annapolis Maritime Museum |
Annapolis Baygrass Music Festival | Sept. 19–20, Sandy Point State Park |
Navy Homecoming vs. North Texas | Oct. 24, Navy-Marine Corps Memorial Stadium |
Maryland Renaissance Festival | Weekends through Oct. 25, Crownsville |
The Annapolis Maritime Museum’s September Sunsets concerts run Thursdays from 6–8 p.m. throughout September and are free, with food trucks and beverages available.
What fall festivals are happening around Annapolis in 2026?
Annapolis Songwriters Festival
From September 10–13, Downtown Annapolis becomes a collection of live-music venues for the Annapolis Songwriters Festival.
One reason we like this event is that you aren’t confined to one venue. You can experience live performances while moving between downtown restaurants, bars, historic streets and the waterfront.
Annapolis Baygrass Music Festival
On September 19–20, Baygrass comes to Sandy Point State Park. The festival combines bluegrass, Americana and jam music with one of the area’s best backdrops: the Chesapeake Bay.
Boatyard Beach Bash
The 21st Annual Boatyard Beach Bash is scheduled for September 19 from 4–10 p.m. at the Annapolis Maritime Museum & Park.
When is the Maryland Renaissance Festival in 2026?
This is a big one for Anne Arundel County.
The Maryland Renaissance Festival celebrates its 50th season in 2026 in Crownsville, just outside Annapolis.
The festival runs:
- August 29–30
- September 5–7, 12–13, 19–20 and 26–27
- October 3–4, 10–11, 17–18 and 24–25
Festival hours are 10 a.m.–7 p.m. each operating day.
It’s one of our favorite recommendations when someone wants something completely different from the typical downtown Annapolis day.
Where are the best pumpkin patches near Annapolis?
Fall around Annapolis also means pumpkin patches, corn mazes and farm trips.
Some places worth putting on your fall list include:
- Homestead Gardens in Davidsonville
- Knightongale Farm in Harwood
- Y Worry Farm in Davidsonville
- Maryland Corn Maze at Sunrise Farm in Gambrills
- Greenstreet Gardens in Lothian
If you’re willing to drive farther, you’ll find additional options around Maryland, including Queen Anne Farm, Councell Farms, Butler’s Orchard and Montpelier Farms.
Local tip: If you’re actually staying in Annapolis, start with Davidsonville, Harwood, Gambrills and Lothian. They’re much more practical for an Annapolis-area fall day than driving across Maryland just for a pumpkin patch.
What are some good fall date ideas in Annapolis?
This might be our favorite part of the guide because Annapolis is an easy place to turn a simple plan into an entire date.
1. Do an Eastport progressive date
Start with coffee or a pastry, walk through Eastport toward the waterfront, and finish with dinner or drinks.
You don’t necessarily need reservations at three different places. The point is to move through the neighborhood instead of spending the entire night at one table.
2. Do Downtown Annapolis at night
Dinner, Main Street, Maryland Avenue, City Dock and a waterfront walk.
Simple, but it’s hard to beat once the weather cools down.
3. Go to a Navy football game and stay downtown
This is one of the most Annapolis-specific fall dates you can do.
Navy has five home games at Navy-Marine Corps Memorial Stadium in 2026:
Date | Opponent |
Sept. 5 | Towson |
Oct. 10 | Tulsa |
Oct. 24 | North Texas, Homecoming |
Nov. 7 | Temple |
Nov. 21 | Memphis |
Make the game only part of the day. Grab something before kickoff and head downtown afterward.
4. Take a golden-hour walk at Quiet Waters
For something quieter, pack food or coffee and head to Quiet Waters Park for an afternoon walk as the leaves begin changing.
5. Have a waterfront picnic at Jonas Green Park
Jonas Green gives you views across the Severn River toward Annapolis and the Naval Academy. Bring food, stay for sunset and keep it simple.
6. Go to the Maryland Renaissance Festival
Yes, it absolutely counts as a date.
And you’ll probably remember it more than another dinner reservation.
When are the Navy football games in Annapolis this fall?
Navy football is part of the rhythm of fall in Annapolis.
The Midshipmen open at home against Towson on September 5, return against Tulsa on October 10, and host North Texas for Homecoming on October 24. Temple comes to Annapolis November 7, followed by Memphis on November 21.
If you’re new to Annapolis, remember that home-game Saturdays can change traffic patterns around the stadium, Rowe Boulevard and surrounding neighborhoods.
But that’s also part of living here.
Where should you get a fall treat around Annapolis?
A fall day isn’t complete without coffee, pastries or something sweet.
A few ideas from our local fall list include Bakers & Co. in Eastport, Black Market Bakers, Sweet Hearts Patisserie, Rise Up Coffee, Curate on West Street, Kilwins on Main Street and Annapolis Ice Cream Company.
And if you’re heading toward Davidsonville for pumpkins, make Homestead Gardens part of the trip and grab some apple cider donuts.
What makes fall in Annapolis different?
It’s the combination.
In the same season, you can watch Navy football, hear live music beside the Chesapeake Bay, walk through Downtown Annapolis, visit a farm, spend an afternoon at the Renaissance Festival and finish another evening watching the sunset over the Severn.
That’s one of the things we love about living here.
Annapolis isn’t only somewhere people visit for a weekend. It’s a place where the things people travel here to experience can become part of your normal life.
Thinking about moving to Annapolis?
If you’re discovering Annapolis because you’re considering living here, we’ve put together another resource specifically for you:
Read next: Moving to Annapolis, Maryland? 10 Things You Should Know Before Buying a Home in 2026.
That guide breaks down neighborhoods, waterfront living, commuting, housing and some of the things we believe buyers should understand before choosing where to live.
I’m Kevin Brown, Team Leader of The Newgen Team, and Annapolis and Anne Arundel County aren’t simply markets we work in. They’re home.
Our goal with guides like this isn’t to constantly sell you real estate. We want our website to become a resource you can come back to when you want to know what’s happening, where to go, where to eat and what it’s actually like to live around Annapolis.
And when life eventually has you thinking about buying or selling a home, we’re here to help.
The Newgen Team
Real People Helping You Through Real Life Moments.
