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Fall things to do in the DMV

September · October · November · DMV seasonal guide

Things to do in the DMV in fall

Great Frederick Fair, leaf peeping, Oktoberfest, In the Street — fall is Frederick’s signature season.

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Why fall is worth the drive

Fall is when Frederick County shines: the Great Frederick Fair, In the Street festival, Oktoberfest tents, apple orchards, and Shenandoah / Catoctin leaf peeping. Pair every outing with a Gabby Rentals SUV or Jeep on Turo — AWD confidence for mountain overlooks and space for friends on festival weekends.

  • Great Frederick Fair week
  • Shenandoah & Catoctin leaf peeping
  • In the Street & Oktoberfest
  • Apple orchards and pick-your-own

Fall itineraries — then book your ride

Location, typical times, and ticket/price guidance for planning — then book the matching Gabby Rentals vehicle on Turo. Always confirm dates and fees for the current year.

Jeep Grand Cherokee for Great Frederick Fair

Frederick Fairgrounds

Great Frederick Fair

Hometown fair energy — rides, food, and exhibits. A local SUV keeps your visit flexible around fair-week traffic.

Location
Great Frederick Fairgrounds, 797 E Patrick St, Frederick, MD 21701
Times & season
Typically mid-to-late September for ~a week (dates change yearly). Gates often open mid-morning; evenings run late for rides and shows. Confirm the current year’s schedule.
Tickets & access
Paid gate admission + ride/show tickets or wristbands. Parking on/near fairgrounds is usually paid during peak nights. Kids/senior discounts often available.
Typical prices
Admission often ~$10–$20 · ride deals extra · parking ~$5–$15

Suggested ride: 2020 Jeep Grand Cherokee · from $89/day

Book Jeep for fair weekOpen in Google MapsOfficial siteJeep Grand Cherokee detailsRelated guide
Jeep Grand Cherokee for Shenandoah & Catoctin leaf peeping

Blue Ridge / Catoctin

Shenandoah & Catoctin leaf peeping

Overlooks, hikes, and cabin weekends. AWD Jeep comfort for Skyline Drive curves and cooler mountain mornings.

Location
Skyline Drive (Shenandoah NP, VA) · Catoctin Mountain Park, Thurmont, MD
Times & season
Peak color often mid-October (elevation dependent). Skyline Drive open 24/7 unless weather-closed; overlooks busiest 10am–4pm weekends. Go weekday or sunrise for fewer cars.
Tickets & access
Shenandoah National Park: vehicle entrance fee (America the Beautiful passes accepted). Catoctin: free. Fog and early freezes can close overlooks — check NPS alerts.
Typical prices
Shenandoah often ~$30/vehicle (7-day) · Catoctin free

Suggested ride: 2020 Jeep Grand Cherokee · from $89/day

Book Jeep for leaf peepingOpen in Google MapsOfficial siteJeep Grand Cherokee detailsRelated guide
Nissan Altima for In the Street Festival

Downtown Frederick

In the Street Festival

Downtown becomes a walkable festival zone. Park once, enjoy stages and food, then leave when the crowds thin.

Location
Downtown Frederick historic district — Market / Patrick Street corridors, Frederick, MD 21701
Times & season
Typically the first Saturday in October, roughly late morning through evening (confirm yearly). Arrive before noon for easier parking; streets close for the festival zone.
Tickets & access
General festival admission is typically free; food, drinks, and some attractions cost extra. Use public garages — expect surge demand.
Typical prices
Free entry · food/drinks $10–$40 · parking $5–$20

Suggested ride: 2019 Nissan Altima · from $53/day

Book Altima for festival dayOpen in Google MapsOfficial siteNissan Altima detailsRelated guide
Nissan Rogue for Frederick Oktoberfest weekends

Frederick area

Frederick Oktoberfest weekends

Tents, music, and friend groups — SUVs make meetups easier. Appoint a driver or keep scenic drives for the next day.

Location
Frederick-area Oktoberfest venues (location can change yearly — verify current site)
Times & season
Usually September–October weekends; sessions may be timed (afternoon/evening entry windows). Buy timed tickets ahead when required.
Tickets & access
Paid admission common; some include a tasting token. Age policies for beer service apply. Designated driver recommended — or visit daytime and tour next morning.
Typical prices
Often ~$15–$40+ admission · food/beer extra

Suggested ride: 2019 Nissan Rogue · from $44/day

Book Rogue for OktoberfestOpen in Google MapsNissan Rogue detailsRelated guide
Toyota Tundra for Apple orchards & pick-your-own

Frederick County

Apple orchards & pick-your-own

Flats of apples and pumpkins need cargo space. The Tundra or an SUV turns harvest weekends into easy hauls.

Location
Orchards & PYO farms across Frederick County / Thurmont foothills (crop-dependent)
Times & season
Apples/pumpkins typically September–October, often daily 9am–5pm or weekends only. Sell-outs happen — check that morning for open fields and last-entry times.
Tickets & access
Usually pay by the pound/bag for fruit; some farms charge a small entry or wagon fee. Containers may be provided or BYO per farm rules.
Typical prices
Often $1–$3+/lb fruit · mini entry fees $0–$10

Suggested ride: 2020 Toyota Tundra · from $76/day

Book Tundra for orchard haulsOpen in Google MapsToyota Tundra detailsRelated guide
Jeep Grand Cherokee for Wine & cider countryside drives

Frederick County / Loudoun

Wine & cider countryside drives

Scenic tasting-room afternoons pair perfectly with fall color — appoint a driver and take the comfortable SUV.

Location
Frederick County & Loudoun County tasting rooms (multiple venues along scenic routes)
Times & season
Many tasting rooms Friday–Sunday plus select weekdays, often 11am/12pm–5/6pm. Reservations recommended on peak foliage weekends.
Tickets & access
Tastings usually priced per person; bottles extra. Follow MD/VA alcohol laws — bring a designated driver.
Typical prices
Tastings often $15–$30 pp · bottles extra

Suggested ride: 2020 Jeep Grand Cherokee · from $89/day

Book Jeep for wine countryOpen in Google MapsJeep Grand Cherokee detailsRelated guide

Fall fleet picks

Real vehicles you can book on Turo for this season’s DMV plans.

View rentals page →

Flying in for a fall trip?

Pair seasonal plans with BWI, Dulles, or Reagan arrival guides.

BWI

BWI Airport

About 45–60 minutes

IAD

Dulles (IAD)

About 45–55 minutes

DCA

Reagan National (DCA)

About 50–70 minutes

Other seasons

Spring

March · April · May

Summer

June · July · August

Winter

December · January · February

Things to Do in the DMV in Fall | Leaf Peeping & Festivals | Gabby Rentals