Best known for its duty-free shops and restaurants, Philipsburg – capital of St. Maarten – is deeply steeped in the history of the Caribbean and European colonial era. A walk down its Front Street thoroughfare will charm guests with delectable restaurants and a plethora of shopping boutiques offering everything from designer clothing, jewelry and cosmetics to authentic Caribbean art and keepsakes, while educating visitors on the profound history of the culturally rich island.

Philipsburg was founded in 1763 by Commander John Philips of the Royal Dutch Navy. It lies between Great Bay and the Great Salt Pond, both of which have fascinating histories in and of themselves. The Salt Pond in particular is of vast significance to St. Maarten’s history as salt harvesting was the primary industry of the island for centuries and the reason for its strategic importance for the imperialistic powers of colonial Europe – including the Dutch, Spanish, French and British – each of which played a role in the island’s history.

Despite its status as St. Maarten’s capital, Philipsburg maintains the charming character of a small Caribbean village. The first stop on any historical tour of Philipsburg is the St. Maarten Museum, which displays numerous artifacts from various eras of St. Maarten’s history, including ancient pottery examples from the Arawak Indians, the island’s original inhabitants. It also features an informative narrative on St. Maarten’s colonial European past as well as cargo salvaged from a British vessel which sank in St. Maarten’s waters in 1801.

The next stop is assuredly the Guavaberry Emporium located right across the street from the St. Maarten Museum. The “Guavaberry” is the key ingredient in the legendary folk liquor of the island, which travelers can sample with free tastings offered to all who stop by this old cedar house which is actually built on the site of an old Jewish cemetery.

The Guavaberry Emporium is the primary retailer of the beloved folk drink, which is made from oak-aged rum and wild Guavaberries and is available in a variety of flavors including Mango, Lime and Spice. The liquor was pioneered centuries ago in private homes and became an integral part of local culture and tradition – it is now a symbol of pride for St. Maarteners.

While Philipsburg is a short drive and an ideal day trip from popular tourist havens such as Maho, Simpson Bay and Dawn Beach, history buffs will want to stay in Philipsburg’s very own Pasanggrahan Royal Guesthouse which is diagonally across the street from the Guavaberry Emporium. The Pasanggrahan Royal Guesthouse is a former Governor’s residence and summer home of Dutch Queen Wilhelmina turned colonial-style hotel.

It is steeped in history and offers a great view overlooking Philipsburg’s Boardwalk and beach in the rear with an old wooden porch in front that is ideal for people watching.

Without a doubt, however, the pinnacle of any walk down Philipsburg’s historic past culminates at the Courthouse, a national symbol that even appears on the country’s flag.

Centrally located in the heart of Front Street, the Courthouse was built in 1793 and originally served as the home of Commander John Philips, Philipsburg’s founder. Since then, the prominent landmark has functioned as a fire station, jail and post office, until its present day use for legal proceedings in St. Maarten.

Architecturally, the wooden structure is painted white with green trim and features a grand cupola topped with a Pineapple which serves as a symbol of “welcome” and “hospitality.”

“The structure is essentially a New England colonial building reminiscent of the 18th century with Creole touches including a New Orleans-style balcony and French doors as well as classical, Neo-Renaissance elements such as quoins,” said Barry Goldsmith, Professor of Architecture at New York University.

Being located in Wathey Square and standing taller than many of the buildings in Philipsburg, the Courthouse is easy to spot and serves as an excellent meeting point for families who split up to pursue their own shopping interests.

Another popular point of interest is The Methodist Church complex consisting of three buildings of historical and architectural interest. The church itself was originally constructed in 1851 and was rebuilt as a replica in 1978.

Other structures in this complex include the “brick building” which was built in the late 1700s to serve as the original Methodist Church but is of part of a school, and “the Manse” which serves as the Minster’s house.

For those fascinated by naval history, there are two forts overlooking Philipsburg – Fort Amsterdam and Fort Willem.

Built in 1631 on a peninsula in Great Bay, Fort Amsterdam is the island’s oldest fort as well as the Royal Dutch Navy’s first military outpost in the Caribbean. It served as a strategic fortification in the Caribbean during the Eighty Years’ War and was captured by the Spanish in 1633.

The Spanish reinforced the fortification and were able to successfully defend it for more than a decade, fending off a major Dutch attack led by Peter Stuyvesant (also a notable figure in New York’s early history) of the Dutch West India Company. Stuyvesant lost a leg in the battle and lived out the rest of his days with a wooden prosthesis, more commonly known as a “pegleg” during the time. Eventually, the Spanish abandoned Fort Amsterdam in 1648 after which it was reclaimed by the Dutch.

Less historically significant but equally fascinating from a visual perspective, Fort Trigge was constructed by the British in 1801 and taken over by the Dutch who renamed it Fort Willem in 1816. A rewarding hike up to the top of Fort Willem offers a scenic panorama of Philipsburg as well as views of St. Barth’s, Saba, St. Eustatius, Nevis and St. Kitts depending on visibility.

“St. Maarten’s history runs deep and includes everything from European colonialism to pirates and indigenous tribal life, but nowhere is this more evident than the streets of Philipsburg,” said May-Ling Chun, interim Director of Tourism for the St. Maarten Tourist Bureau. “It is without a doubt the cultural center of St. Maarten and a crucial component of any vacation to the island.”