Chestertown Maryland Hotels & Motels

When Chestertown, MD Shines Brightest: Your Seasonal Travel Guide

Chestertown, MD experiences distinct climate particularities throughout the year, making it a versatile destination for the outdoorsy type. In spring, the town comes alive with blooming flowers and mild temperatures, perfect for exploring the scenic trails in nearby parks or taking a leisurely stroll along the waterfront. Summers in the area are warm and sunny, offering ideal conditions for boating, kayaking, and enjoying the Chesapeake Bay. The famous Chestertown Tea Party Festival, held in May, is a notable event that commemorates the town's colonial past with reenactments, parades, and a boat race. Fall brings stunning foliage and cooler temperatures, creating a picturesque backdrop for visiting local farms and orchards or attending the Downrigging Weekend Tall Ship and Wooden Boat Festival. Held in November, this festival showcases a fleet of tall ships and classic wooden boats, offering visitors the chance to sail on the Chesapeake Bay and experience maritime history up close. The festival also features live music, maritime exhibits, and delicious food vendors, creating a festive atmosphere for all to enjoy. Winters in Chestertown are mild, and the holiday season brings festive events such as the Dickens of a Christmas celebration in December. No matter the season, the town offers a diverse range of open-air activities, cultural celebrations, and natural beauty, making it a year-round destination worth exploring.

Hotel Savings: Best Discount Offers in Chestertown, MD

Numerous hotels in the Chestertown area offer promotions that make traveling more affordable for different groups of guests, including extended stay discounts for those who wish to linger a little longer. With special rates for large groups, family vacations or gatherings can be more cost-effective. Our programs, in partnership with global hotel chains, ensure that guests enjoy great prices for all types of bookings, whether you're an individual traveler or part of a larger group. AAA members, for instance, can benefit from better cancellation policies, complimentary breakfasts, and room upgrades. Military personnel and senior citizens often have access to exclusive discounts, making their trip more affordable without compromising the quality or range of amenities. Whether it's a budget-friendly or a luxury property, there are ways to save while enjoying a memorable holiday in Chestertown.

Community Spirit of Chestertown: Top Festivals and Events

Every year on Memorial Day weekend, Chestertown, MD comes alive with the Chestertown Tea Party Festival. Commemorating a defiant act similar to the Boston Tea Party, the festival kicks off with a parade featuring music, dance, and puppet shows, leading to a dramatic re-enactment where locals, dressed as Continental Soldiers and angry citizens, toss tea into the Chester River from the schooner Sultana, after a mock battle with "British" soldiers. But the fun isn't only for history buffs; the town also hosts a lively First Friday event each month. Residents and visitors from nearby areas flock to Main Street, where local shops like "Walnut & Wool", "The Finishing Touch", and "Twigs and Teacups" welcome everyone. The sidewalks buzz with people, including students from Washington College, as they explore the unique items on display. Whether you're stepping back in time or enjoying the contemporary community spirit, Chestertown's events offer a blend of history and culture that's sure to enchant.