Insider's Guide to an Outdoorsy Weekend in Hilton Head

Watersports, like Stand Up Paddle boarding, are a staple of the outdoor scene at Hilton Head
Watersports, like Stand Up Paddle boarding, are a staple of the outdoor scene at Hilton Head Outside Hilton Head
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As the sun climbs toward the horizon on the South Carolina shore, and its first bright rays stretch across the rolling ocean, a wonderful alchemy begins to takes place on Hilton Head Island. The cool, steel blues and grays of pre-dawn transform to the golden tones of early sunrise. The waves, like most things here, are gentler in these parts: coming in not so much with a crash, but more of a melodic whoosh.

Sitting on your balcony, watching this scene unfold, it's easy to imagine whiling away the morning with a second cup of coffee. But even here, where visitors and transplants immediately notice a slower pace of life, an abundance of outdoor adventure awaits. It’s not the strenuous, hike-up-a-mountain or battle-class-IV-rapids kind of excursion, but it can easily fill a long weekend. And it’s uniquely Hilton Head in its subtle style.

Here's what to see, do, and eat—and more—for an active-minded weekend in Hilton Head.

The Sea Pines Nature Preserve teems with amazing wildlife.
    Rob Glover
The Sea Pines Nature Preserve teems with amazing wildlife. Rob Glover

Saturday

Sea Pines is a huge resort area and home development on the southern tip of Hilton Head Island. As an early innovator of building with a focus on preserving green space in the 1950’s, the Fraziers—the original developers of Sea Pines—set aside several hundred acres of land that would become the Sea Pines Nature preserve.

Accessing the resort and nature preserve requires passing through a gate and paying a small fee. Once through, Sea Pines opens up like a town unto itself. For some pre-adventure fuel, stop at the bustling Harbour Town Bakery and Cafe. The case at the front of the cozy coffee shop is crammed with the most decadent pastries imaginable. The pecan sticky buns are half the size of a dinner plate and topped with a gooey, caramel-y concoction.

The Harbour Town Bakery and Cafe is home to huge pastries and great coffee.
    Rob Glover
The Harbour Town Bakery and Cafe is home to huge pastries and great coffee. Rob Glover

Nature Preserve Boat and Bike Ride Throughout the Sea Pines Forest Preserve preserve, Spanish moss drips from gnarly hardwood trees, hiding huge osprey nests that can weigh hundreds of pounds. Towering pines and the ever-present palmetto tree, with its crown of pointy green leaves, huddle together in tight stands. A 6-foot alligator, a holdover from the time of the dinosaur, lounges on the shore of Lake Joe. Indeed, walking the trails of the preserve, you half-expect a T-Rex to poke its snout through the dense vegetation.

The best way to begin an exploration of the prehistoric looking preserve is with a boat tour of Lake Thomas. (Actually, this is the only way to see the preserve by water if you don’t own a house here, as use of watercraft is restricted to residents.) The guide will point out an elegant night crane, teach you about the alligators that call these lakes home, and help you get oriented for the rest of your time here.

Touring on land is best done on two wheels. (Rental shops abound around town, but one recommended outfitter is Outside Hilton Head, with two locations.) Some of the nature trails in the preserve are open to foot traffic only, but convenient racks make it easy to lock up your bike for these short strolls. Maps are easy to follow and lead you to the highlights of this distinctly beautiful place.

The lakes may appear to be a natural part of the terrain but were actually created during the first phases of modern development and provide a safe haven for the island's animal inhabitants. Dating back to its antebellum agricultural days, the Old Lawton Rice Field is now an ideal spot to spy egrets and heron from a raised observation deck. Just south of the rice field, the Vanishing Swamps—whose fluctuating waters give the swamp its name— also harbors their share of avian inhabitants.

One of the island's most visible signs of early human occupants, meanwhile, is the Shell Ring, a remarkable testament to the island's inhabitants thousands of years ago. Accessible via an easy 0.4-mile walk through gnarly live oak and palmetto trees, the ring is a circular deposit of decaying shells, left by early Indians some 4,000 years ago.

The resteraunts that line Reilley's Plaza, like the Lodge, offer a wide variety of food and drink
    Courtesy of Hilton Head Island Visitor and Convention Bureau
The resteraunts that line Reilley's Plaza, like the Lodge, offer a wide variety of food and drink Courtesy of Hilton Head Island Visitor and Convention Bureau

Lunch Options at The Triangle

Reilley’s Plaza, also known among locals as “The Triangle”, is a centrally located destination for laid-back dining and refreshments, with a range of choices for most tastes. The smell of smoky BBQ emanates from One Hot Mamas, the “pit-to-plate” pulled pork and rib specialists. Across the walkway, the inviting atmosphere of Reilley’s Grill and Bar combines elements of a proper Irish pub with an open-air feel common to the island, plus huge cuts of prime rib and traditional fish and chips. The incredible list of local, regional, and international craft beer at The Lodge, located just behind Reilley’s, makes this the place for quality pub grub with a neighborhood bar feel.

Stand-Up Paddleboarding

Outside Hilton Head offers SUP and kayak rentals and lessons for water exploration all over the island
    Outside Hilton Head
Outside Hilton Head offers SUP and kayak rentals and lessons for water exploration all over the island Outside Hilton Head

It’s no surprise that much of the outdoor adventure available on a low-lying island happens on the water. What many first-time visitors find surprising, however, is that there is so much variety. Rivers, salt marshes, and, of course, an ocean all bring different elements to a fulfilling day of paddling.

A good way for beginners to get their feet wet in the local SUP scene is with a 90-minute beginner paddleboarding lesson from Outside Hilton Head. Launching from the Shelter Cove Marina on the Broad Creek, the classes cover the basics of paddleboarding—strokes, standing, and balance. But instructors leave ample time for exploring the grassy wetlands of the Harbor River, where swift gulls and graceful heron fly overhead, looking for snacks in nearby oyster beds. The shop also offers advanced classes and rentals, as well as a well-stocked retail space.

Dinner on Hilton Head: A Pescatarian’s Delight

Crab cakes and shrimp are must-haves at The Olde Oyster Factory
    Rob Glover
Crab cakes and shrimp are must-haves at The Olde Oyster Factory Rob Glover

After watching crafty birds harvest their dinner from the abundant waters of Hilton Head, it’s time to sample a bit of the bounty yourself. Every local has a favorite spot, but some long-standing stalwarts of the seafood scene always make the list.

Hudson’s Seafood House on the Docks began as a fishing operation in the 1960s and has served the freshest possible shrimp, oysters, and soft-shell crab ever since, complete with beautiful views of Port Royal Sound in the dining room. Arrive early, though, as Hudson’s fills up fast and does not take reservations.

Another Hilton Head favorite with amazing sunset views, The Olde Oyster Factory has been serving their namesake delicacy for over 25 years. Spend time on the spacious dock, soaking up an idyllic low country scene, before digging into your meal. Start with a crab cake appetizer, but save room for shrimp, served fresh from local waters and prepared in several different ways. One can't miss-option is the low country boil: Mixed with andouille sausage, corn on the cob, and red potatoes, the shrimp are moderately seasoned, allowing their natural sweetness to come through.

Sunday

With finely packed sand, few other people, and a gorgeous sunrise, dawn is the best time of day for a run or ride on the beach
    Rob Glover
With finely packed sand, few other people, and a gorgeous sunrise, dawn is the best time of day for a run or ride on the beach Rob Glover

Sunrise Run on the Beach

Hilton Head is a runner’s paradise: The island is even shaped like a running shoe, with Sea Pines occupying the toe. It seems impossible for a land mass that’s just 42 square miles to have so many stretches of uninterrupted running opportunity, but 60 miles of biking/jogging paths weave their way through the pine and palmetto of Hilton Head. The natural surface trails of Sea Pines Forest Preserve and Pickney Island provide a softer alternative to paved pathways. And the beach, well, that’s an experience in itself.

When dampened by a retreating tide, the fine grain sand surrounding much of Hilton Head Island packs into a fantastically dense running surface. The island sees a huge tide differential, meaning at low tide there is a wide surface area with plenty of room for all runners and bikers.

Two locations on the island make a stop at the Palmetto Running Company a convenient way to grab gear and beta for your Hilton Head jog.
    Rob Glover
Two locations on the island make a stop at the Palmetto Running Company a convenient way to grab gear and beta for your Hilton Head jog. Rob Glover

Ideally, your accommodations will be adjacent to one of Hilton Head’s beaches so you can lace up, or kick off, your shoes and go. If not, Palmetto Running Company , the two location-hub for walkers, joggers, and marathoners on the island, suggests two prime spots to get in a long run. Burkes Beach in the north is a little more laid back and quiet, located near the “heel” of the island. But the waves here can be a bit bigger, making for some interesting scenery. Down south, somewhere near the “ball” of the foot-shaped island, Coligny Beach , along with adjacent beaches, stretches far enough to really get the sweat going during a morning run. This is a very busy public beach, so get going early. Take advantage of free public parking across the roundabout from the entrance to Coligny Beach Park.

Fuel-Up Options

Low Country Backyard has perfect outdoor dining
    Rob Glover
Low Country Backyard has perfect outdoor dining Rob Glover

Low Country Backyard has perfected the practice of outdoor dining. The backyard, covered by a giant umbrella and tucked between the restaurants two indoor seating spaces, is a quiet haven of iron tables, eclectic knick-knacks, and a small porch that serves as the stage for frequent live music evenings.

The Backyard doesn’t offer breakfast during the week, so the weekend brunch is a great way to experience the cozy eatery (most evenings, it's full of folks waiting for favorites like seafood purloo—pan sautéed shrimp and smoked sausage—or potato-chip meatloaf.) Highlights of the brunch menu include bananas foster waffles and variations of eggs Benedict. The Backyard Benedict features a hearty base of homemade buttermilk biscuits with layers of sausage, hash brown casserole, and poached eggs, topped with a kicky sausage gravy.

Biking is a great way to tour the Hilton Head. Bike paths cover Sea Pines and Pinckney, and connect most of the island.
    Rob Glover
Biking is a great way to tour the Hilton Head. Bike paths cover Sea Pines and Pinckney, and connect most of the island. Rob Glover

Food might be the last thing on your mind after Low Country Backyard, but be sure t0 stop at the Purple Cow on the way out to Pinckney Island for snacks to fuel the rest of the day's exploration: Fresh-from-the-oven mini coffee cake and the French toast donuts are can't miss favorites.

The creative mind behind the Purple Cow is also the genius of Baby Cakes mini cheesecakes, which come in flavors like toasted marshmallow and key lime. One is the perfect size for a quick snack—so you should get two, because, you know, vacation calories.

Pinckney Island National Wildlife Refuge

The ponds of Pinckney Island Nature Preserve are a haven for thousands of the areas water loving birds
The ponds of Pinckney Island Nature Preserve are a haven for thousands of the areas water loving birds Jeff Gunn

It’s time for a little island-hopping, and one to definitely add to the list is Pinckney Island National Wildlife Refuge , a 4,000-acre conservatory of low country flora and fauna. Fourteen miles of trail connect salt marsh, tidal creeks, forests, grasslands and ponds.

The ponds, manmade in the 1950s, are certainly the highlight here. They attract thousands of birds, creating an outdoor aviary of sorts. Any one tree growing from the aptly named Ibis Pond, for example, may hold a dozen of the large, brilliant white birds. Heron, storks, and egrets launch and land from the island—a freshwater oasis for birds, turtles, and even a few alligators.

Between these avian sanctuaries, the flat, grass, or crushed-rock paths pass under towering pine forest and through vast stretches of grasslands. Many of these trails are not directly shaded, so an early-morning or late-afternoon visit will avoid hours spent in direct sunlight. Pinckney is an ideal place for a long run, too, but many visitors find biking the best way to reach all the best spots.

Dinner Options

Fat Patties is a great dinner option after exploring Pinckney Island.
    Rob Glover
Fat Patties is a great dinner option after exploring Pinckney Island. Rob Glover

Since you’re already on this side of the river, Fat Patties in Bluffton is an easy stop for a filling dinner. As its name suggests, the star of this menu is the hamburger. Their venerable version of an American classic begins with a half-pound of ground beef (you can get a 5-oz “skinny pattie” or substitute for chicken, shrimp, turkey or black bean) and is paired with a substantial list of toppings, including inspired options like mango bean salsa, brie, and creole remoulade.

The beer list is almost as impressive as the burger toppings. Selections change often, but there’s a good variety of craft options from around the country. For a super-local suds sampler, though, you’ll want a flight from Salt Marsh Brewing, which features styles from the super light Weiss to the deep, rich porter, brewed 30 feet above the bar at Fat Patties.

Where To Stay During a Weekend in Hilton Head

Even the most adventurous traveler needs a rest now and then. The Sonesta Resort offers lots of ways to get it.
    Courtesy of Hilton Head Island visitors and Convention Bureau
Even the most adventurous traveler needs a rest now and then. The Sonesta Resort offers lots of ways to get it. Courtesy of Hilton Head Island visitors and Convention Bureau

Visitors outnumber year-round residents of Hilton Head by more than 60 to 1, which explains the wide variety in lodging. Huge houses and small bungalows are plentiful throughout the island, and motels offer an option for budget-conscious travelers.

When possible, basing yourself along one of Hilton Head’s beaches is a great way to access the best amenity on the island. The Sonesta Resort on Hilton Head offers direct access to wide, ocean-facing beaches from a convenient location midway down the island. The entire property invites exploration with turtle-filled lagoons, tropical gardens, and a multitude of cozy cabanas, porches, decks, and docks. For a true Hilton Head experience, rent bikes from the resort and ride the beach in the morning and the shady paths that meander around the area in the afternoon.

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