A Daytripper’s Guide to Block Island

Our favorite way to see Block Island in one budget-friendly day.

As a kid, I used to spend weekends out on Block Island helping — though they might use a different word — my grandparents run their bed and breakfast in New Harbor. When I wasn’t turning down sheets or picking wildflowers for guest bouquets, I often watched days turn into nights from a sandy spot with a clear view to Point Judith.

Then, during my summers off from college, I returned to the Island to work at a T-shirt shop and lived in free employee housing right in the center of town — not a bad place to make memories. All that time, it was really difficult for me to understand why so many of my friends and classmates never make it out for a visit.

But now, fully submerged in adulthood, I get it. Unless you have a place to stay, it can be tough to justify a several-night trip to Block Island. Vacations to the Cape or New Hampshire cost about the same and probably feel more like a getaway — at least you’ve left the area code. But, after visiting on Memorial Day weekend, I realized the tiny, seven-by-three-mile island can be thoroughly explored in one thoughtful day, and on the cheap.

Many island businesses participate in the Taste of Block Island in spring and fall. With the purchase of a $5 button, visitors get unheard-of deals at restaurants, shops, salons and even bike rental businesses. Follow the insider’s itinerary below, and you’ll pack in more of the Island’s scenic beauty, shopping and tasty food than you could imagine.

9 a.m. Board the Block Island Ferry in Point Judith. Purchase your Taste of Block Island button on the boat and enjoy a breezy view from the top deck.  

10 a.m. Arrive on-island. Head over to the Seacrest Inn at the corner of High Street and Weldon’s Way (behind the movie theater) for discounted bike rentals.  

10:30 a.m. Take your new set of wheels over to Froozies Juice Bar and Cafe, through the back courtyard at the National Hotel (the big white one at the end of the main drag) for a healthy breakfast burrito and coffee for $9.99. The pesto, mozzarella and baby spinach burrito, a personal favorite, should fuel you up for the next leg of your trip.

11:15 a.m. Time to hit the road on the least-hilly route around the Island. About nine miles; a leisurely two- to three-hour route with stops.

  • Head out of Froozies and take a left on Ocean Avenue. Follow the road past the Block Island Grocery and head up a (small) hill to the intersection of Ocean and Beach avenues.
  • Take a right, then a quick left, to stay on Ocean Avenue. Notice a boat basin on your right.
  • At the end of Ocean Avenue, keep left to follow the route — or stay straight and you’ll wind up on Payne’s Dock, home of the killer doughnuts. You might just have to buy one.
  • Back on route now, continue to follow West Side Road. The Oar restaurant, the Old Harbor Boat Basin and the Great Salt Pond should be on your right. Directly across the street is Red Gate Farm, where my grandparents once ran a bed and breakfast. Say hello to the cows for me.
  • After a mile or so of biking, you’ve officially entered the West Side of Block Island, where many Island residents live year-round. Keep an eye out for Dories Cove Road on the right. Bike down the dirt road and visit the secluded pebbly beach where residents flock during the high season. When you visit again on an overnight trip, this is where you should have your bonfire. The views of the sunset from this west-facing beach are phenomenal.
  • About one mile later, West Side Road ends on Cooneymus Road. Take a right on Cooneymus, and keep your eyes peeled for the entrance to Rodman’s Hollow on the right. If you’ve got the energy, bike down Black Rock Road to a wooden turnstile at the trailhead. The hike through the hollow is about three miles.
  • Return to your bike and continue East on Cooneymus Road, which ends at a Native American cemetery intersecting on Lakeside Drive. Poke around the cemetery for an eerie history lesson, then return to the road and head south on Lakeside Drive, with the backside of Rodman’s Hollow and Fresh Pond on your right. This is one of my favorite stretches on Block Island. Between the sparkling pond and historic stone walls cutting through the landscape, it really feels like a different time and place.
  • Lakeside Drive turns onto Mohegan Trail Road at the Painted Rock, a quirky feature of the island where tourists and residents frequently cover the rock with birthday wishes and the occasional marriage proposal.
  • Stop off at the first overlook for the Mohegan Bluffs on the right — often referred to as Second Bluffs by locals — for an incredible view of the Atlantic. There’s another bluffs overlook shortly thereafter, complete with a steep staircase of about 150 steps down to the beach.
  • Keep traveling on Mohegan Trail Road and you’ll spot the Southeast Lighthouse, which in 1993 was moved 300 feet back from the cliffs to protect the historic structure from the effects of erosion.
  • Mohegan Trail Road then turns into Spring Street, and it’s all downhill from here. See a gorgeous view of the ocean on the right and the sweeping lawns of the Spring House Hotel on your left.

2 p.m. Return the bikes to Seacrest Inn, which is visible at left from the stop sign at the end of Spring Street. Head back to Water Street, the main drag across from the ferry. Right across the street from the National Hotel is a small, steep access point to Crescent Beach. Take the path and walk the beach down about a quarter of a mile. You’ll see the Beachhead restaurant to your left on Corn Neck Road.

2:15 p.m. Time for lunch. Feast on the Beachhead’s outside deck overlooking the beach with a lobster salad roll, the Corn Neck calamari or a cup of the Block Island clam chowder. Get 10 percent off with the Taste of Block Island Button.

3:30 p.m. Walk the beach back to town and visit some of Water Street’s quaint shops.

  • Get your Block Island T-shirt, trinket or sticker fix at Star Department Store, directly across from the ferry landing. The Taste of Block Island button earns you 10 percent off your total purchase.
  • Across the street from Star, visit the Glass Onion, an excellent gift and home decor shop. The shop sells Island Mist all-natural bath and body products. I’d recommend the lavender mist to just about anyone. Get 10 percent off selected items with a Taste of Block Island button.
  •  Circumnavigate the Star Department Store building on the right via Chapel Street and visit East of the River Nile Trading Company, a cool little shop that boasts wares from around the world. To boot, owner Ron Munschy is one of the friendliest faces around. Get 10 percent off your purchase with a Taste of Block Island button.
  • Tucked in a nook next to Eli’s Restaurant — more on that later — which is to the right of East of the River Nile, you’ll find Blocks of Fudge, a great place to pick up a Block Island-made treat for friends or family.

6 p.m. For a quick bite before you board the 7 p.m. ferry, head to the bar at Eli’s Restaurant for the best tuna nachos in history and a melt-in-your-mouth warm goat cheese and arugula salad. Get 10 percent off your purchase with a Taste of Block Island button.

6:45 p.m. Take Chapel Street back to the ferry landing (you can see the docks from the front door at Eli’s) to board the 7 p.m. boat, and wave goodbye to Block Island, at least for now.

The Taste of Block Island is held in spring and fall. Buttons are available for purchase aboard the Block Island Ferry and at the Block Island Chamber of Commerce, located in the ferry parking lot. Visit blockislandchamber.com for more information.

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