Anne Arundel County Maryland Maryland Avenue Fall Festival

On the third Sunday of October, two blocks of Maryland Avenue in historic downtown Annapolis fill with stalls, music and families out for the afternoon. The Maryland Avenue Fall Festival takes over the first two blocks of the avenue, between State Circle and Cumberland Court, for a single day of local vendors, food trucks, live music, a beer garden, antiques, handmade goods, children’s activities and a Halloween Pup Parade. The 2026 edition fell on Sunday 18 October, running from ten in the morning until five in the afternoon, rain or shine. Entry costs nothing: two local-events layers print “Free Admission” for visitors. The organiser is the Maryland Avenue and State Circle Business Association, printed in some layers as the Maryland Avenue and State Circle Association, and the organiser layer bills the gathering as one of the longest-running festivals in the state.

About

The Maryland Avenue Fall Festival is a neighbourhood street fair with a long run behind it, set on a short stretch of one of downtown Annapolis’s historic streets. The festival closes the first two blocks of Maryland Avenue to traffic for the day so that vendors, performers and visitors can spread out along the pavement. This is not a fairground event behind a fence: the street keeps its shopfronts while the stalls go up in front of them.

Annapolis is the seat of Anne Arundel County, and the avenue sits in the historic downtown. Local vendors sell crafts and goods, food trucks serve lunch, a beer garden offers a place to sit with a drink, and live music runs through the day. Children have activities of their own, and the Halloween Pup Parade brings dogs in costume down the avenue, a fitting touch for a festival that falls in the second half of October. The parade is one element among many.

The event is also printed as the Maryland Ave Fall Festival and as the Maryland Avenue and State Circle Fall Festival. The Inner West Street Association and the Downtown Annapolis Partnership are named in the layers as partners for the Scarecrow Stroll, a separate downtown event, and they are not organisers of this festival. This one belongs to Maryland Avenue and its businesses.

Quick Facts

Detail	Information
Festival name	Maryland Avenue Fall Festival
Host town	Annapolis, Maryland
County seat	Annapolis is the seat of Anne Arundel County
Venue	First two blocks of Maryland Avenue, between State Circle and Cumberland Court, historic downtown Annapolis
Organiser	Maryland Avenue and State Circle Business Association
Latest dated edition	Sunday 18 October 2026, ten in the morning to five in the afternoon, rain or shine
Earlier dated editions	Sunday 19 October 2025; Sunday 20 October 2024
Admission	Free to enter; vendor spaces charged at one hundred dollars and food truck spaces at eighty dollars
Programme highlights	Local vendors, food trucks, live music and performances, beer garden, antiques, handmade goods, kids activities, Halloween Pup Parade
Also billed as	Maryland Ave Fall Festival; Maryland Avenue and State Circle Fall Festival

History

The layers repeat a claim to longevity without pinning down a start date. The organiser layer bills the festival as one of the longest-running in the state, and a local-events layer billed the 2025 edition as the festival’s fifty-fourth year. Both statements are recorded as the layers print them, and no founding year is derived from the billing.

For a useful comparison, see the Anne Arundel County Maryland Maryland Seafood Festival for another county festival.

Three dated editions are documented in the layers read, and they fall in a steady pattern. The 2024 edition took place on Sunday 20 October, recorded in a tourism press-release layer. The 2025 edition took place on Sunday 19 October, from ten in the morning until five in the afternoon, and was billed as the fifty-fourth year in a local-events layer. The 2026 edition took place on Sunday 18 October, at the same hours, rain or shine, according to the organiser layer. Each of those three dates is the third Sunday of October in its year.

The name has stayed steady while its printings have varied. The sheet title, “Maryland Avenue Fall Festival”, is printed exactly in a local-events layer and a tourism layer. “Maryland Ave Fall Festival” shortens the avenue’s name, and “Maryland Avenue and State Circle Fall Festival” widens it to take in the circle at the head of the avenue. All three printings name the same event, and the organiser’s name varies the same small way, between the ampersand form and the “and” form. The festival has stayed on Maryland Avenue while other events have come and gone.

What to Expect

A visit to the Maryland Avenue Fall Festival is a walk down two blocks of a historic street lined with stalls. Local vendors set out handmade goods and crafts, and antique sellers bring pieces that suit the old street. Food trucks park along the avenue, so lunch is a matter of choosing between them. The beer garden gives adults a place to pause with a drink, and live music runs through the day.

Kids activities are listed in the programme, and the Halloween Pup Parade is the part of the day most likely to draw a crowd to the kerb. Dogs in costume walk the avenue with their owners, giving the festival a light-hearted centre that fits the October date.

The hours are short and fixed: ten in the morning until five in the afternoon, as recorded for both the 2025 and 2026 editions. Seven hours is enough to walk both blocks slowly, browse, eat and watch the parade. The festival runs rain or shine, so a wet forecast does not cancel the day. There is no gate and no ticket to enter: two local-events layers print “Free Admission”, and the only charges recorded are the fees paid by stallholders. A visit costs whatever a visitor chooses to spend at a stall, a food truck or the beer garden.

Planning Your Visit

The festival occupies the first two blocks of Maryland Avenue between State Circle and Cumberland Court, so head for Maryland Avenue itself: the two blocks are easy to walk end to end. Arriving near the ten o’clock opening gives the quietest hour for browsing, while midday is busiest. The festival closes at five, so an afternoon arrival still leaves several hours on the street.

Entry is free, so there is nothing to book and no ticket to buy in advance. Carry the ordinary things for a day outdoors: comfortable shoes, a layer for the October air, and something for rain, since the festival goes ahead rain or shine.

The site is a flat street rather than a field, the hours are short, and the children’s activities and the pup parade give younger visitors something to look forward to. Owners who bring a dog for the parade should expect a street full of people and other dogs. Visitors who want a longer day can pair the festival with a walk around the historic downtown. The layers give no parking directions, so drivers should expect limited street parking on a festival day.

Sample Itinerary

Start at ten in the morning, when the stalls are freshly set and the street is at its calmest. Walk the full length of both blocks first, from State Circle toward Cumberland Court, to see what the vendors have brought; the antique tables and handmade goods repay a slow look.

By late morning, settle in for the music, then drift toward the food trucks for lunch. The beer garden is a natural pause in the middle of the day. After lunch, take the children to the activities, and keep an eye on the time for the Halloween Pup Parade.

The last hour is for the purchases that need a second look: go back to the stalls that stood out, pick up the piece still on your mind, and walk the avenue once more as the five o’clock close approaches. By then the stalls are packing up and the street is returning to itself.

How It Compares

Annapolis holds more than one autumn event, and the Maryland Avenue Fall Festival is easy to confuse with two of them. The Annapolis Fall Harvest Festival takes place at the Pip Moyer Recreation Center, away from Maryland Avenue, with its own venue and programme. The two share a season and a city, and nothing else that the layers record.

The Annapolis Scarecrow Stroll is closer in spirit and in geography, since it is also a downtown event. But the Scarecrow Stroll is a separate event from the Maryland Avenue Fall Festival, with its own identity and its own organisation. Those partnerships explain why the same names appear in the layers for both, but they do not make the two events one.

Two blocks is a modest footprint, filled without spilling into the wider downtown. Larger Annapolis events spread across many venues or run for several days; this one is a single street for a single day, from ten until five. Everything is within a short walk, the whole programme is visible from the pavement, and a visitor can take in the entire festival in an afternoon.

Checklist

• Head for Maryland Avenue between State Circle and Cumberland Court, in historic downtown Annapolis
• Arrive near ten in the morning for the quietest browsing, or in the afternoon for the liveliest street
• Wear comfortable shoes for walking on pavement, and bring a layer for the October air
• Carry something for rain, since the festival runs rain or shine
• Bring a bag for purchases from the vendors, antique sellers and craft stalls
• Keep time free for the Halloween Pup Parade, the day’s most popular single event
• Plan lunch around the food trucks, and allow a pause in the beer garden
• Remember that entry is free, so the only spending is what you choose at the stalls
• Allow time after the five o’clock close for a walk around the historic downtown

Beyond the Festival

Maryland Avenue sits in historic downtown Annapolis, and the streets around it carry the same eighteenth-century shape that gives the old city its character. A walk beyond the two festival blocks takes a visitor past shopfronts, old houses and the circles that organise the downtown plan, and the waterfront is a short walk away. The festival is a good reason to come downtown; the downtown itself is a good reason to stay.

Annapolis is the seat of Anne Arundel County and the capital of Maryland, and its downtown is a working place as well as a historic one. The shops and restaurants near the festival are open on festival day, and many visitors combine the street fair with a meal or a browse. Free entry makes that easy: a visitor can move between the festival and the rest of downtown without feeling tied to one place. The autumn timing adds cooler air and early colour, and the Pup Parade nods to the season without making the day about Halloween alone.

Why It Matters

The Maryland Avenue Fall Festival matters first of all to the street it is named for. A street fair gives the businesses along Maryland Avenue a day when the avenue itself is the attraction, bringing people to shopfronts they might otherwise walk past. The organiser is the avenue’s own business association: the people who work on Maryland Avenue put on the event that fills it.

It matters to Annapolis for a second reason: the long run the organiser layer claims. A festival billed as one of the longest-running in the state, and in its fifty-fourth year in 2025, has been part of the city’s autumn for longer than most of its visitors have been coming to it. Street events often change hands or stop altogether; this one has stayed on its two blocks.

It also matters as a free, open event in a city with a crowded calendar of ticketed occasions. Two local-events layers print “Free Admission”, and the open street means anyone in downtown Annapolis on the third Sunday of October can walk into it. A free street fair asks nothing of a visitor except attention.

Frequently Asked Questions

What part of Annapolis hosts the Maryland Avenue Fall Festival?

The festival takes place on the first two blocks of Maryland Avenue, between State Circle and Cumberland Court, in historic downtown Annapolis. The avenue is closed to traffic for the day, with the stalls, food trucks, beer garden and performances along those two blocks.

Does walking into the festival cost anything?

No. Two local-events layers print “Free Admission”, and visitors pay nothing to enter. The only charges recorded in the layers are vendor fees: one hundred dollars for a vendor space and eighty dollars for a food truck space. What a visitor spends at the stalls, food trucks and beer garden is their own choice.

What can families with children do at the festival?

The programme includes kids activities, and the Halloween Pup Parade is a highlight for younger visitors, with dogs in costume walking the avenue. The festival is a flat, walkable street open from ten until five, and the food trucks and live music give families plenty to do between the children’s activities.

Does the festival go ahead in wet weather?

Yes. The 2026 edition was billed rain or shine, and the festival goes ahead whatever the weather brings. Visitors should dress for the forecast, since the whole event takes place outdoors on the street.

What to Expect From the Next Anne Arundel County Maryland Maryland Avenue Fall Festival

How often is Anne Arundel County Maryland Maryland Avenue Fall Festival held?

The festival is an annual event, held once a year on a Sunday in October. The three dated editions fell on Sunday 20 October 2024, Sunday 19 October 2025 and Sunday 18 October 2026, each the third Sunday of October in its year.

When is the next Anne Arundel County Maryland Maryland Avenue Fall Festival?

The latest edition with a published date is Sunday 18 October 2026, from ten in the morning until five in the afternoon. A date for a following edition has not appeared in the material consulted, and the pattern points to the third Sunday of October as the time to watch for.

Will the dates change?

The date has stayed on the third Sunday of October across all three dated editions, and the hours have stayed at ten until five for the two most recent. The organiser sets the date for each edition, so visitors should check the organiser’s own announcements nearer the time.

The Maryland Avenue Fall Festival is a small festival with a long history, and its appeal is the simple one of a good street on a good day: two blocks of a historic avenue, filled with stalls, music, food and neighbours, open to anyone who walks in.