Cesis
Cesis is the quintessential old world town in Latvia. It is nestled among rolling hills, giving it a beautiful, fantasy world like setting. The small town is sprinkled with old castles, fortresses, and parks that you can leisurely wander through to pass the time. There's a lovely town square that is the perfect place to grab a seat on a bench and people watch. Because of the square's central location, many residents pass through it on their way to and from the market. The town is intertwined with lovely cobblestone streets that are lined with old homes, in various stages of disrepair. Cesis manages to perfectly balance a level of authentic wear and tear with a fairytale ambiance. Outside of town you'll find great hiking trails so that you can explore the rolling hills and picturesque countryside. The small town is also conveniently located less than 100 kilometers from Riga, making it an easy trip on a bus.
There are some wonderful sights around town, many of which highlight the towns history. Make sure you visit Saint Johns Church, Victory Monument, the Square of Roses, May Park, and of course the Medieval Castle.
There are some wonderful little restaurants around town that offer traditional Latvian dishes. Several have attached bakeries that sell wonderful fresh breads and deserts that can perfectly round of the meal.
The ideal time to visit Cesis is during the summer months when the weather is at its warmest and the hiking trails are more appealing. Spring and fall can also be nice but weather can change abruptly so don't be surprised if it's cold while you're there. Also understand that during the low season many hotels and restaurants will be closed so your options will be limited. It can be nice to be in the area when the tourist crowds are at a minimum. It offers you a glimpse into true Latvian culture.