Oakland Maryland Main Street

03/09/2026

🗳️ It’s Election Day in Oakland!

Today’s the day to make your voice heard! Stop by the polls, cast your vote, and take part in shaping the future of our community.

Local elections help guide the direction of our town, so every vote truly counts. Whether you head there first thing in the morning or swing by later today, we encourage everyone who’s eligible to participate.

While you’re out, take a stroll through downtown, visit a local shop, or grab a bite to eat—supporting our community is always a good idea!

Polls are open today—don’t forget to vote! 🇺🇸🗳️

The Town of Oakland will hold its annual election on Monday, March 9, 2024.  The polls will be open from 9:00 AM to 6:00 PM. Voters will enter the Council Chambers by the side door to vote.  One candidate will be elected as Mayor for a 2-year term, and three candidates will be ele

02/19/2026

Ice sculptures ✔️
Wine samples ✔️
Shopping bags ✔️
Smiling faces everywhere ✔️

Winterfest and the A&E District Wine Walk brought the energy downtown this weekend — and you all showed up in the best way!

Main Street Oakland knows how to celebrate. 🍷❄️

Tag yourself, tag your friends, and tag your favorite Main Street business below!

&EDistrict

02/13/2026

❄️🎉 Winterfest is tomorrow! 🎉❄️

Join us in the Main Street District February 14 for a full day of Winterfest fun — ice sculptures, shopping, family activities, and the A&E District’s Wine Walk!

To keep everyone safe during the celebration, please see the street closures below for the duration of the event:

We appreciate your patience as Main Street fills with visitors. Plan ahead, drive carefully, and come enjoy Winterfest!

See you on Main Street! ☃️✨

02/09/2026

Can't wait to spend the day on Oakland, MD Main Street!

Love is in the air… and downtown ❄💗
Celebrate Winter Fest on Main Street, Oakland, this Saturday, February 14!

Ice sculptures, sweet treats, kids activities, sleigh rides, shopping, music — and a Wine Walk for the adults 🍷

A perfect winter day in our favorite small town.

02/05/2026

Only 9 days away! Early Bird Tickets available until Friday, February 13!

OAKLAND — The Town of Oakland invites residents and visitors alike to celebrate Valentine’s Day with Winter Fest, a celebration of “winter magic” on Saturday, Feb. 14, in the downtown

01/15/2026

Welcome to Oakland, MD Main Street!

We’re proud to be a Designated Main Street organization dedicated to preserving Oakland’s historic charm, supporting local businesses, and bringing our community together through events, culture, and economic growth.

From seasonal festivals and downtown events to small business support and historic preservation, our mission is to keep downtown Oakland vibrant, welcoming, and thriving for residents and visitors alike.

Follow us to stay up to date on:
✨ Upcoming events
🏪 Local business highlights
🏛️ Preservation & revitalization projects
🤝 Community partnerships

Small Town Charm, Big Heart.
We’re glad you’re here!

📸 Share your downtown photos and tag us!
📅 Watch for event announcements and ways to get involved.