Our Events

Downtown Dover comes alive year-round with signature events that celebrate art, culture, and community. From Paint Dover to Winterfest and more to come; this is your place to learn what’s happening downtown and connect to event details.

October 15 – 19, 2025 – Registration Now Open! Paint Dover 2024

Paint Dover! is a plein air painting event and art competition in downtown Dover, Delaware, with three days of painting options, culminating in an artwork exhibition, competition, and sales to the public.

Participating Paint Dover! artists from around the region take to the streets, parks, sidewalks and outdoor cafes to participate in this annual event in the cooler fall season. Inspired by downtown Dover’s architectural landscape, historic commercial buildings, gardens and scenery, artists quickly capture changing light and shadows, and the “spirit” of downtown Dover. The community is invited to watch artists paint outdoors throughout the three days, attend the exhibition, and purchase artwork.  Over $1,000 in awards are presented!  An extended exhibition takes place virtually and downtown

January 16-17, 2026 – Details Coming Soon!

Formerly Fire & Ice Festival, Winterfest is Downtown Dover’s signature winter celebration. A bold and cozy mix of ice, fire, food, and fun. It’s a chance to experience the heart of Dover in an unforgettable way, bundled up, lit up, and full of small-town magic.

Fire Pits & Live Entertainment

Live Ice Sculpting Demos

Outdoor Vendors & Hot Drinks

Family-Friendly Activities

October 15 – 19, 2025 – Registration Now Open! Paint Dover 2024

Paint Dover! is a plein air painting event and art competition in downtown Dover, Delaware, featuring three days of painting options, culminating in an exhibition, competition, and public sales.

NEW THIS YEAR – Two-Hour Quick Draw is Sunday, October 19th.

REGISTRATION NOW OPEN – CLICK HERE

Interested in Purchasing a Painting?

View an exhibition and purchase a 2025 painting at The Biggs Museum of American Art:  Sat-Sun, October 18-19, 2025!

Or contact the Downtown Dover Partnership via email at Diane@DowntownDoverPartnership.com

 

Thank you to the partners and sponsors of Paint Dover! 2024

Biggs MuseumBLICK Art SuppliesCity of DoverDE Division of the ArtsDel-One FCUDover Art LeagueJerry’s Artarama of DelawareNational Endowment for the ArtsBayhealthAffordable Business Systems and PNC Bank

Last Year’s (2024) Award Winning Paintings

Paint Dover is a competition in which the artists compete for $2,000 in awards. This year, winners included:

  • Mayor’s Choice:  Karen Mcgloughlin
  • Curator’s Choice – 1st Place:  Quenna Mast
  • 2nd Place:  Trish Doty
  • This is Dover!:  N. Taylor Collins
  • Stately Homes:  Trish Doty
  • Dover Heritage:  Robert Manning
  • Iconic Loockerman:  Katie Mundie
  • Small Works:  Cathy King
  • Small Works:  Teresa Rodriguez
  • Small Works:  Cheryl Wisbrock

 

View the Virtual Exhibition from 2024