The Pühalepa Church is Hiiumaa’s oldest stone church. In 1255, the German Order started the construction of a stone fortress-church. Initially lacking a steeple, the arched stone church was completed in the 14th century, but the construction of the steeple was not started until 1770.
During the Livonian war (16th century) the Pühalepa church was plundered, but it was restored again at the beginning of the 17th century. At least it is said that the Scottish admiral Clayton, who died of plague in 1603 in Hiiumaa, was buried in the church with dignity. In the first quarter of the 17th century, the Danes plundered the church.
In 1636 the landlords of Hiiessaare (named Gentschien) donated a gorgeous stone pulpit to the congregation (rare anywhere in Estonia), thus buying themselves the right to be buried in the church choir-room. Their tombstone stands by the southern window of the choir-room.
The Soviet period was just as costly to the church as was the Livonian war. During the occupation, the church was closed, the benches were cut out, the organ was smashed and the church was turned into a warehouse. After independence was regained, the church also recovered. Now the congregation once again owns the church and most of the former church property has been returned. The altarpiece that was lost during the war has been replaced by a colourful stained glass. Services and concerts are held regularly in the church.
Glimmingehus is the best preserved medieval stronghold in Scandinavia. It was built 1499-1506, during an era when Scania formed a vital part of Denmark, and contains many defensive arrangements of the era, such as parapets, false doors and dead-end corridors, 'murder-holes' for pouring boiling pitch over the attackers, moats, drawbridges and various other forms of death traps to surprise trespassers and protect the nobles against peasant uprisings. The lower part of the castle's stone walls are 2.4 meters (94 inches) thick and the upper part 1.8 meters (71 inches).
Construction was started in 1499 by the Danish knight Jens Holgersen Ulfstand and stone-cutter-mason and architect Adam van Düren, a North German master who also worked on Lund Cathedral. Construction was completed in 1506.
Ulfstand was a councillor, nobleman and admiral serving under John I of Denmark and many objects have been uncovered during archeological excavations that demonstrate the extravagant lifestyle of the knight's family at Glimmingehus up until Ulfstand's death in 1523. Some of the most expensive objects for sale in Europe during this period, such as Venetian glass, painted glass from the Rhine district and Spanish ceramics have been found here. Evidence of the family's wealth can also be seen inside the stone fortress, where everyday comforts for the knight's family included hot air channels in the walls and bench seats in the window recesses. Although considered comfortable for its period, it has also been argued that Glimmingehus was an expression of "Knighthood nostalgia" and not considered opulent or progressive enough even to the knight's contemporaries and especially not to later generations of the Scanian nobility. Glimmingehus is thought to have served as a residential castle for only a few generations before being transformed into a storage facility for grain.
An order from Charles XI to the administrators of the Swedish dominion of Scania in 1676 to demolish the castle, in order to ensure that it would not fall into the hands of the Danish king during the Scanian War, could not be executed. A first attempt, in which 20 Scanian farmers were ordered to assist, proved unsuccessful. An additional force of 130 men were sent to Glimmingehus to execute the order in a second attempt. However, before they could carry out the order, a Danish-Dutch naval division arrived in Ystad, and the Swedes had to abandon the demolition attempts. Throughout the 18th century the castle was used as deposit for agricultural produce and in 1924 it was donated to the Swedish state. Today it is administered by the Swedish National Heritage Board.
On site there is a museum, medieval kitchen, shop and restaurant and coffee house. During summer time there are several guided tours daily. In local folklore, the castle is described as haunted by multiple ghosts and the tradition of storytelling inspired by the castle is continued in the summer events at the castle called "Strange stories and terrifying tales".