Stay at The Still Pond Inn
for Chestertown Tea Party

May 22-24, 2026

Use Code TEAPARTY for 20% Off Your Stay

Planning a trip for the Chestertown Tea Party? The Still Pond Inn is a charming place to stay just 15 minutes from historic Chestertown, with easy access to the parade, reenactments, waterfront events, shopping, food, and the famous tea toss. Spend the day enjoying the festivities, then come back to comfort, quiet, and a more relaxing pace at the inn.

The Chestertown Tea Party is one of the Eastern Shore’s signature spring events, bringing visitors to town for a lively weekend of history, tradition, and family-friendly fun. From historic reenactments and the colonial parade to artisan vendors, local food, live music, and the famous tea toss, the festival fills downtown Chestertown and the waterfront with energy and charm.

After a day exploring High Street and the Chester River, The Still Pond Inn puts you within easy reach of the weekend’s festivities while offering a more peaceful place to stay. Located on Maryland’s Eastern Shore, our inn is a natural choice for guests who want to experience the excitement of Chestertown during the day and slow down in a more relaxed setting at night.

2026 Chestertown Tea Party Festival Highlights

Friday, May 22
Kick off the weekend at Wilmer Park with a free street party from 5:00–9:00 PM featuring live music from The Doug Segree Band, local food trucks, and a beer wagon. At dusk, fireworks light up the waterfront in celebration of America’s 250th anniversary.

Saturday, May 23
Saturday is the heart of the festival. A free parking shuttle runs from 8:00 AM–5:00 PM, making it easy to explore town.

• 8:00 AM: Tea Party Distance Classic / Run for Radcliffe
• 9:00 AM: Heritage Village opens on the Court House Lawn
• 9:00 AM: Food and artisan vendors open throughout downtown
• 10:00 AM: Colonial Parade along High Street
• 2:00 PM: Historic reenactment from the main stage to the waterfront
• 4:00 PM: Vendors close

From High Street to the Chester River, the entire town fills with energy, history, and local charm.

Sunday, May 24
The celebration continues at Wilmer Park with a more relaxed but lively waterfront atmosphere:

• Noon: Beer Fest begins with craft beer tasting and live music
• Artisan vendors, food trucks, and children’s activities throughout the day
• 2:00 PM: Raft race coverage
• 2:30 PM: Raft race begins on the waterfront
• 4:00 PM: Festival concludes

Whether you’re visiting for Saturday’s main events or planning a full weekend getaway, The Still Pond Inn makes it easy to experience the best of the Chestertown Tea Party—and then slow things down at your own pace.

With scenic drives, historic towns, waterfront views, and a relaxed Eastern Shore atmosphere, the area is especially appealing for couples, weekend travelers, and anyone looking to turn the festival into a memorable getaway.