Best events in
Oakland

Looking for events or things to do in Oakland, FL? This quiet town is defined by its small-town charm, community-focused gatherings, and deep connection to its natural surroundings. While nightlife is minimal, the local rhythm revolves around family-friendly festivals, outdoor recreation along the West Orange Trail, and easy access to the amenities of nearby Winter Garden.

The Historic Town Center acts as the community's heart, hosting markets and seasonal celebrations at the Healthy West Orange Arts & Heritage Center.
Oakland’s abundant green spaces, including Speer Park and VanderLey Park, provide scenic backdrops for annual traditions and free concert series.
For nature-centric activities, the Oakland Nature Preserve offers a full calendar of environmental education programs, hikes, and the yearly Nature Fest.

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Nearby cities

Orlando

15 miles away

Lakeland

41 miles away

Winter Park

17 miles away

Altamonte Springs

17 miles away

Sanford

27 miles away

Kissimmee

22 miles away

Maitland

16 miles away

Winter Garden

3 miles away

University

26 miles away

Winter Haven

37 miles away

Four Corners

16 miles away

Alafaya

27 miles away

St. Cloud

30 miles away

Deltona

35 miles away

Clermont

7 miles away

DeLand

38 miles away

Pine Hills

10 miles away

Orange City

33 miles away

Oviedo

27 miles away

Fairview Shores

14 miles away

Longwood

20 miles away

Ocoee

7 miles away

Apopka

12 miles away

Leesburg

23 miles away

Wesley Chapel

47 miles away

The Villages

32 miles away

Coleman

32 miles away

Mount Dora

17 miles away

Casselberry

20 miles away

Horizon West

8 miles away

Orlando

15 miles away

Lakeland

41 miles away

Winter Park

17 miles away

Altamonte Springs

17 miles away

Sanford

27 miles away

Kissimmee

22 miles away

Maitland

16 miles away

Winter Garden

3 miles away

University

26 miles away

Winter Haven

37 miles away

Four Corners

16 miles away

Alafaya

27 miles away

St. Cloud

30 miles away

Deltona

35 miles away

Clermont

7 miles away

DeLand

38 miles away

Pine Hills

10 miles away

Orange City

33 miles away

Oviedo

27 miles away

Fairview Shores

14 miles away

Longwood

20 miles away

Ocoee

7 miles away

Apopka

12 miles away

Leesburg

23 miles away

Wesley Chapel

47 miles away

The Villages

32 miles away

Coleman

32 miles away

Mount Dora

17 miles away

Casselberry

20 miles away

Horizon West

8 miles away

Online Events

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Sat, Oct 17 • 9:00 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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Thu, Nov 5 • 1:00 PM GMT

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Thu, Nov 12 • 2:00 PM UTC

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Sat, Dec 19 • 8:00 PM EST

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Wednesday • 7:00 PM GMT+1

Check ticket price on event

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Thursday • 1:00 PM GMT+1

Check ticket price on event

Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Sat, Oct 17 • 9:00 AM EDT

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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Thu, Nov 5 • 1:00 PM GMT

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Thu, Nov 12 • 2:00 PM UTC

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Sat, Dec 19 • 8:00 PM EST

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Events near Oakland

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REWIND ⏪: Orlando’s #1 Throwback Block Party | 90s, 2000s & Early 2010s ✨

Sat, Oct 17 • 1:00 PM

Wall Street Plaza

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LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

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Romantasy BookCon- Orlando 2026

Thu, Oct 22 • 4:00 PM

Hilton Orlando Lake Buena Vista - Disney Springs Area

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TASTE OF AFRICA MUSIC AND FOOD FESTIVAL

Sat, Oct 24 • 2:00 PM

Eagle Nest Park

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R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

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2026 Pastors & Leaders Conference

Wed, Nov 11 • 4:00 PM

Hilton Orlando Buena Vista Palace Disney Springs Area

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DYLAN GOSSETT w/ BUFFALO TRAFFIC JAM - APOPKA

Sat, Nov 21 • 6:00 PM

Apopka Amphitheater

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FanGrrrl Romance Recs Premier Book Signing 2027

Thu, Sep 2 • 6:00 PM

Hilton Orlando

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REWIND ⏪: Orlando’s #1 Throwback Block Party | 90s, 2000s & Early 2010s ✨

Sat, Oct 17 • 1:00 PM

Wall Street Plaza

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LEMON DROP & SEAFOOD FESTIVAL

Sun, Oct 18 • 4:00 PM

Wall Street Plaza

Check ticket price on event

Romantasy BookCon- Orlando 2026

Thu, Oct 22 • 4:00 PM

Hilton Orlando Lake Buena Vista - Disney Springs Area

Check ticket price on event

TASTE OF AFRICA MUSIC AND FOOD FESTIVAL

Sat, Oct 24 • 2:00 PM

Eagle Nest Park

Check ticket price on event

R&Boo: Orlando’s First Ever Halloween R&B Block Party

Sun, Oct 25 • 4:00 PM

Walter's Tavern

Check ticket price on event

2026 Pastors & Leaders Conference

Wed, Nov 11 • 4:00 PM

Hilton Orlando Buena Vista Palace Disney Springs Area

Check ticket price on event

DYLAN GOSSETT w/ BUFFALO TRAFFIC JAM - APOPKA

Sat, Nov 21 • 6:00 PM

Apopka Amphitheater

Check ticket price on event

FanGrrrl Romance Recs Premier Book Signing 2027

Thu, Sep 2 • 6:00 PM

Hilton Orlando

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Frequently asked questions about Oakland

Are there free events to attend in Oakland, FL?

Yes, Oakland offers several free community events throughout the year. The Music Under the Oaks series in VanderLey Park provides free concerts each autumn, and seasonal celebrations in the Historic Town Center are open to all.

Where can I find live music events in Oakland?

VanderLey Park is the primary spot for live music during the annual Music Under the Oaks concert series. For more frequent live entertainment and a wider variety of venues, residents often visit the neighboring town of Winter Garden.

What are some family-friendly things to do in Oakland?

The town specializes in events for all ages, centered on its parks and public spaces. Annual gatherings include the Heritage Day Festival at Speer Park and the festive Santa's Lane transformation of the town center.

What kind of outdoor events happen at the Oakland Nature Preserve?

The Oakland Nature Preserve hosts many nature-focused events for the community. Its calendar includes the annual Nature Fest, environmental education activities, and seasonal guided walks like the Pumpkin Glow nighttime jack-o'-lantern hike.

Does Oakland host any art festivals or events?

Yes, Oakland celebrates local arts with a few key events. The community gathers for the Annual Town of Oakland Arts & Music Festival, and the Healthy West Orange Arts & Heritage Center regularly features local art exhibits.

What is the nightlife like in Oakland, FL?

Oakland's evenings are generally quiet and relaxed, reflecting its family-oriented community. For more active nightlife with a larger selection of restaurants and breweries, most locals make the short trip to nearby Winter Garden.

When and where is the Oakland Farmers Market held?

The Oakland Farmers Market takes place on the second and fourth Thursdays of each month. It is held at the Healthy West Orange Arts & Heritage Center, offering fresh produce and handmade goods from local vendors.

How can I plan a relaxed date night starting in Oakland?

A great date can begin with a walk or bike ride on the West Orange Trail. Afterwards, check for an outdoor concert at VanderLey Park or head into the more bustling downtown Winter Garden for dinner and drinks.

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Nearby cities

Orlando

Lakeland

Winter Park

Altamonte Springs

Sanford

Kissimmee

Maitland

Winter Garden

University

Winter Haven

Four Corners

Alafaya

St. Cloud

Deltona

Clermont

DeLand

Pine Hills

Orange City

Oviedo

Fairview Shores

Longwood

Ocoee

Apopka

Leesburg

Wesley Chapel

The Villages

Coleman

Mount Dora

Casselberry

Horizon West

Orlando

Lakeland

Winter Park

Altamonte Springs

Sanford

Kissimmee

Maitland

Winter Garden

University

Winter Haven

Four Corners

Alafaya

St. Cloud

Deltona

Clermont

DeLand

Pine Hills

Orange City

Oviedo

Fairview Shores

Longwood

Ocoee

Apopka

Leesburg

Wesley Chapel

The Villages

Coleman

Mount Dora

Casselberry

Horizon West

Online Events

How To Be Kind To Yourself - Shahroo Izadi

HBR Book Webinar: Resilient Optimism

Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

(ONLINE) Women on the Move with Ann Patchett

Witch hunts and real lives

No Title, No Permission, No Problem: Harnessing the Power of Influence

Lean Global Connection 2026

Washington Crossing the Delaware / The Crossing - Film History Livestream

How To Be Kind To Yourself - Shahroo Izadi

HBR Book Webinar: Resilient Optimism

Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

(ONLINE) Women on the Move with Ann Patchett

Witch hunts and real lives

No Title, No Permission, No Problem: Harnessing the Power of Influence

Lean Global Connection 2026

Washington Crossing the Delaware / The Crossing - Film History Livestream