Block Island, 13 miles (21 km) south of the South County shore of Rhode Island at Port Galilee (map), is a time capsule from the 19th century. Much of the Victorian-era architecture has been preserved, and new buildings have kept to the island style.
All businesses on the island—hotels, restaurants, cafés, shops, banks, car rental—are local. There are no formula or chain businesses such as Avis, Dollar Store, Hilton or Starbucks, just local folks doing business and keeping the money on the island.
You can't imagine how refreshing this is until you've experienced it.
Day Trip or Overnight?
The island is eminently manageable, being only seven miles (11 km) long at its longest point. You can enjoy a lot of the island on a day trip, more if you stay overnight, and all of it if you stay for few days or a week, perhaps in a Victorian-era hotel or vacation rental apartment (see below).
Getting to Block Island
Hi-speed Block Island Ferry m/v Athena waits for passengers at Port Galilee RI.
The ferry voyage to Block Island (30 to 55 minutes) is pleasant enough, with plenty of room to sun on the top-deck benches, and a small bar and snack counter on board.
New England Airlines (tel 401-596-2460), "Block Island's resident airline," flies to Block Island from Westerly RI daily in summer.
As you approach Block Island, the character of the place becomes clear: sand dunes and tawny cliffs, low shrubs and grass with a few trees, ponds, and hillocks (highest point on the island is 211 feet/64 meters above sea level). And beaches all around!
Ferries from Port Galilee RI
Port Galilee (Point Judith), Rhode Island, is the port with the most frequent ferry service, with six to nine daily sailings in summer by the traditional Block Island Ferry (cars, passengers, bikes) and additional sailings by the Hi-Speed Ferry (passengers & bikes, no cars), in each direction from mid-June to early September. Sailing time is less than an hour, though the entire trip takes longer because of embarking and debarking.
Traditional Car Ferry
Passengers and bicycles need no reservations, but to ship a car or motorcycle you must have reservations in advance—well in advance! January, when reservations are first available, is not too early to book. By late spring, most voyages may be fully booked. Because of limited space on ferryboats to transport private cars, taking taxis and renting cars on the island are wise alternatives to bringing your own car.
You can book your passenger and bike ticket(s) online, but if you do, you must specify a sailing time and you cannot change it. If you buy your ticket(s) at the Galilee ticket office, however, you can take any boat, anytime. Ferries rarely fill up, so this is normally possible, and preferred. Busiest times for the ferries are beginnings and ends of weekends, particularly holiday weekends.
The Galilee agent is the Block Island Ferry, Galilee State Pier, Point Judith RI 02882 (tel 866-783-7340 or 401-783-4613). Get to the Galilee dock at least 45 minutes before sailing time.
During spring, fall, and winter the car ferry makes fewer trips: two daily in each direction in May and early June, and late September through October; in winter, there's one trip daily.
There is also high-speed ferry service by Block Island Ferry from Galilee. The high-speed catamaran ferry carries passengers and bikes only (no cars), and makes the voyage in about 30 minutes, though tickets are more expensive than on the traditional car ferry. No reservations required. Get to the Galilee dock at least 45 minutes before sailing time.
Parking for all these ferries is fairly easy, with many private lots near the docks charging about $10 per calendar day, perhaps $15 on weekends.
Ferry from Fall River MA & Newport RI
The Block Island Ferry also operates daily summer Hi-Speed Ferry service to Block Island from Fall River MA (State Pier, 1 Water Street near Battleship Cove), and Newport RI (Perotti Park, 39 America's Cup Avenue (see the map above).
The Hi-Speed Ferry carries passengers and bicycles only, no motor vehicles. The voyage from Fall River to Newport takes an hour, then another 75 minutes from Newport to Old Harbor, Block Island.
Seating is limited, so advance reservations (click here) are recommended.
Ferry from New London CT
Block Island Express operates passenger-ferry service in summer between the New London Ferry Dock at 2 Ferry Street, New London, CT 06320 (map), within a five-minute walk of New London's Union Station for Amtrak trains, and the Greyhound Bus Station (map), meaning that you can take a train or bus from New York City, the Connecticut Shoreline, Providence or Boston to New London, then a ferry to Block Island.
You can also take the Cross Sound Ferry (cars & passengers) from Orient Point, at the eastern tip ofLong Island NY, to New London, then transfer to the Block Island Express (passengers only) ferry to reach Block Island.
On Block Island, the ferry arrives at Old Harbor.
Old Harbor & New Harbor
Block Island, officially incorporated as the town of New Shoreham RI in 1672 (here's more history), has two settlements. Old Harbor is the larger, with docks for the ferries from Galilee/Point Judith RI and New London CT; and New Harbor, with several marinas, one of which (Champlin's Marina & Resort) serves as the dock for ferries from Montauk (Long Island) NY.
The Block Island Chamber of Commerce Visitor Center, right by the ferry dock in Old Harbor.
The big old Victorian hotels come almost down to the water in Old Harbor, presenting a proud first view of the island to visitors arriving on the ferries to Old Harbor.
Several of the more distant hotels have vans which will be waiting at the dock to pick up passengers who have reservations, or those who want a room but have not reserved; and there is a taxi rank at the dock as well.
Most of the island's buildings— houses as well as hotels— date from the late 1800s or early 1900s.
On Block Island the pace is relaxed, and islanders have a strong sense of community.
Block Island is relatively small, just 7 miles (11 km) from north to south. This makes walking a possibility, bicycling a delight, and mopeds a practical means of transport.
Walking, biking, moped, taxi and rental car are all used to get around on Block Island. Most of the roads, excepting the paved main road around the island, are rough and sandy (nobody has to be in a hurry to get quickly from one end of the island to the other).
Traffic on Block Island
Block Island's roads are single-lane and two-lane only, with some sidewalks but no bikepaths, so bicycles, mopeds, cars, trucks and in some places pedestrians all share the roadway. This usually works pretty well. Here are some tips:
—Pedestrians have absolute priority and right of way
—Bicycles are next. They must stop for pedestrians, but mopeds and larger vehicles must defer to bicycles. When biking on the island, follow all traffic regulations and signal your turns.
—Mopeds, often driven by first-time moped users, must take special care not to cause accidents.
—Car and truck drivers must keep in mind that all people and all vehicles share the roads equally.
You can bring your own bicycle with you on some of the ferries. If you don't, just bring your helmet and rent a bike from any of a dozen shops in town on the island.
Bicycles on the ferry to Block Island: bring your own, or rent one in Old Harbor.
You'll see some bike and moped rental shops in Old Harbor even before you land. Others are hidden away on back streets. Lots of choices!
A moped is any sort of small motorbike. The ones on Block Island tend to be motor scooters, comfortable to ride and capable of seating two persons.
Think carefully before you rent and ride a moped! Most visitors who rent a moped, motor scooter or motorcycle have never ridden one before. They hit the road after only the briefest of lessons from a rental shop. Thus, every summer brings a number of moped accidents with bodily injuries, a few of them serious.
Helmets are included in moped and motor scooter rentals on Block Island. Use them!
If you rent a two-wheeled motor vehicle, be particularly cautious, especially after the first hour or two of riding. Accidents often happen soon after you think you've mastered the vehicle and the roads.
Your rental agreement will stipulate that you may not drive the rented vehicle on unpaved roads, which is a disadvantage on Block Island, as many beaches are reached by unpaved roads. (Bicycles may ride on unpaved roads.)
Also, some roads are off-limits to mopeds by town ordinance because of safety concerns. This road goes to Mansion Beach, one of Block Island's finest beaches—but you can't go there on a moped.
You'll see taxis waiting at the dock or the airport when you arrive on Block Island. They're a practical way to get around if you haven't brought or rented your own vehicle.
No national/international car rental companies have agents on Block Island. Two local businesses rent cars. The cars may not be as new or shiny as what you're used to from the big companies, but on such a small island, you won't be spending more than a few minutes in the car on any given trip.
—Block Island Bike & Car Rental, tel 401-466-2297, 834 Ocean Street, rents bikes and cars (no mopeds or jeeps).
Where to Stay
You'll see them as you approach Old Harbor in New Shoreham, Block Island by ferryboat: these wonderful big old Victorian-era hotels with clapboards, mansard roofs, and cupolas flying the American flag.
Spring House Hotel, up on a hill with fabulous views.
Most have been renovated and the facilities modernized, but the century-old ambience and character are carefully retained.
There are other wonderful, pictureque hotels, inns and B&BS inland from the ferry docks: the 3-star Hotel Manisses, the 45-room National Hotel, the Block Island Beach House—"the only hotel right on the beach"—and Payne's Harbor View Inn in New Harbor.
They look old-fashioned, but they are quite up-to-date when it comes to rates, however. You can check rates and availability on this handy Hotel Map with Prices, which includes mainland hotels if you plan to visit Block Island on a day-trip:
Because demand for rooms in summer is high, you should be sure to have reservations in advance during high season (from mid-July through Labor Day).
Save on Weekdays!
You can save 10% to 20% on many lodging establishments if you stay during the week (Monday through Thursday) instead of the weekend if your schedule allows it.
Breakfast is (Usually) Included
On Block Island, most hotels serve breakfast to their guests at no additional charge. Breakfast may be anything from pastries and coffee to a full all-you-can-eat buffet.
Taxes & Service Charges
Also, all hotel prices are subject to the Rhode Island 11% sales plus room tax, and some hotels levy a service charge (usually 4% to 6%) in place of your tips to the staff. Ask about taxes and service charges when you make your hotel reservation to avoid hotel bill shock when your bill turns out to be 11% to 15+% more than you anticipated.
Beware of Fog on Flights!
If you plan to fly to Block Island, be aware that fog may cause cancellation of your flight. You should plan your schedule so that in the event of bad weather you will still be able to catch a ferry and get to your hotel in time to claim your reserved room. If you don't make it, you will forfeit your deposit and your reservation.
What to See & Do
Most people coming to Block Island are looking for an easy schedule, quiet relaxation, time at the beach, bicycle trips, and lobster dinners.
Bordered nearly all around by fine white sand, Block Island is beachgoers' heaven. You can walk from Old Harbor and the ferry dock to a good beach in a few minutes. Most others are within a fun bike ride
Stuff NOT to Do
New Shoreham town ordinances prohibit camping anywhere on the island (except Scout groups, etc), sleeping overnight in cars or on beaches, riding motorcycles on the beaches, and shellfishing without a license. Dogs must be leashed at all times.
A Bit of History
In 1614 a man named Adriaen Block visited a small island off the coast of Rhode Island, and he gave the island his name. Slightly over 20 years later a colonist was found dead in a boat near the island, presumed murdered by the local Pequot people and this unhappy event precipitated a battle between Pequots and colonists which turned out to be very bloody.
A generation later, these events forgotten, settlers from the colony moved onto the island (1661), a settlement was built, and incorporated as the town of New Shoreham in 1672.
The official name and incorporation of Block Island is still the Town of New Shoreham. To be scrupulous about it, when you visit Block Island, you are touring the town of New Shoreham.
For almost 200 years the people of New Shoreham lived their quiet lives, fishing in boats from the island's two natural harbors, growing what they could in the sandy and windswept soil.
In the mid-1800s the Age of Steam changed Block Island from a fishermen's outpost in the Atlantic to a summer excursion paradise, with regularly scheduled steamboats bringing residents of the sooty factory cities out for fresh air and bright sunshine.
Late-19th-century frame hotels, sprawling and spacious, went up to accommodate them, and the island's economy came to depend on tourism rather than fishing, and so it has remained. Most of the island's buildings—houses as well as hotels—date from the late 1800s or the turn of the century.
The Harborside Inn in 2019. Sadly, it suffered a disastrous fire in August 2023.
In New Shoreham
At some point in the day, you'll want to relax in a café or restaurant with a view of the harbor and the sea. A few small art galleries and craft shops are good for a browse., and the island has a cinema and a number of cocktail lounges and night clubs, mostly in the hotels.
Twilight scene on Block Island.
Only about a mile northwest of Old Harbor along Ocean Avenue and West Side Road just west of Legion Park (map) is the island's cemetery, with headstones dating from the 1600s and 1700s. It's a pretty spot, and interesting to anyone intrigued with Block Island's history.
On Block Island you're never far from a beach—you can debark from the ferry in Old Harbor and be on the beach in two minutes—but each beach has its advantages and disadvantages.
There's no shade on any of the beaches, so bring your own shelter. Lifeguards? Only at Fred Benson Town Beach.
The wide crescent that forms most of the eastern shore of the island is all beach, mostly broad and sandy, with some surf. The western and southern shores can be stony both in and out of the water, but they are uncrowded and more private.
Crescent Beach is the colloquial name for the entire long crescent of sand stretching northward several miles from Old Harbor on Block Island's eastern shore, on the eastern side of Corn Neck Road (map). This long beach is popularly divided into several sections named Kid Beach, Fred Benson Town Beach, Scotch Beach, Mansion Beach, etc.
Right in Old Harbor
The harbor is framed by Ballard's and Kid beaches, right there in the middle of town.
Just east of the Old Harbor breakwater, behind Ballard's Restaurant (map), Ballard's Beach has drinks served by restaurant staff, organized games like beach volleyball, and a lively crowd of regulars.
Kid (Baby) Beach
At the very southern end of Fred Benson Town Beach, Kid Beach (or Baby Beach) is only a short stroll north from Old Harbor, with gentle waves, an easy slope, and moderate water temperatures: perfect for little kids.
Fred Benson Town Beach
The most popular beach on Block Island, sometimes called by its former name of State Beach, has fine white sand, gentle surf, all beach services, lifeguards, and is walking and biking distance from Old and New harbors.
The long beach along the eastern shore of Block Island north of Old Harbor is the island's most accessible and popular place for sand, sea, sun and fun.
Fred Benson Town Beach, on Corn Neck Road (map), is a wide, level beach of fine white sand with a gentle incline into the sea and enough low surf to keep it interesting.
The water temperature is moderate. The surf may carve small pools out of the sand: perfect for the little ones.
All the services are here: parking, toilets, showers, snacks, lifeguards, rentals of beach umbrellas, cabanas, beach chairs and boogie boards.
Fred Benson Town Beach is where many teenagers and families hang out.
Walk or drive north a short distance to Scotch Beach and Mansion Beach and the crowd changes to families and older couples. There are no services on these more northerly sections of the beach, but parking is allowed along the road parallel to the beach.
The northward extension of Fred Benson Town Beach is farther from the services, but quieter and more popular with tranquil couples and small families.
Even farther north than Scotch Beach, Mansion Beach is good for getting away from the crowds while still enjoying the fine sand and other beauties of Block Island's eastern shore. Mopeds are not allowed on the unpaved beach access road, but bikes and cars are fine.
The beaches on the south shore of Block Island are sand, pebbles, stones and rocks backed by the Mohegan Bluffs, the sandy cliffs along the island's southern shore (map). They're not the same as the smooth, wide, white sand beaches backed by grass-covered dunes of the eastern shore. To reach the southern beaches you must descend 150 stairs (at Payne's Overlook) or clamber down rough paths. The beaches tend to be rocky onshore and off, so caution is necessary when entering the water.
Payne's Overlook Stairway
A few hundred yards west of Southeast Lighthouse is Payne's Overlook, with a parking area, bike rack, overlook point, and a stairway descending 150 steps to a small beach that's never crowded.
Reached by a narrow ankle-breaker path through Snake Hollow near Barlow's Point (map), Vail Beach is rocky, sandy, surfy and never crowded.
To reach Vail Beach you must pick your way among the ruts and rocks on a narrow path down Snake Hollow (map), not a particularly easy walk, and not easily doable with lots of beach paraphernalia. (There's no shade on the beach, so you'll need an umbrella or shelter.)
Your reward is a relatively little-visited beach in a more dramatic setting. Sit for awhile, perhaps with a book or pair of binoculars; look for good camera angles; walk, think, sing to yourself; take a dip in the cool water—that's the Vail Beach experience.
Bring whatever you need—especially water, and shade if you need it—and carry out your trash. There are no services whatsoever here.
Black Rock Beach
Reached by rough trail through Rodman's Hollow, this beach is named for a sinister black rock offshore, covered by water, that is a deadly danger to ships. Backed by cliffs, the beach is rocky and surfy, for adventurers only.
Dorry's Cove Beach
On Block Island's western shore, Dorry's Cove is a small dark-sand beach reached via Dorrys' Cove Road. Good for swimmers, snorkelers and picnickers.
This long beach on Block Island's western shore reached by an unpaved road has no services, but lots of sand and no crowds. If you like fishing from shore, this is the place for you.
Charleston Beach is long, stretching from the inlet to New Harbor south along the western shore of Block Island to Dorry's Cove Beach (map).
Narrower and rougher than the smooth sand beaches on the island's eastern shore, Charleston has some coarse sand, pebbles and stones, but few people.
You can reach this beach by bike or car along Champlin Road. The first access point has no car parking, but plenty of room for bikes.
Farther along to the north there are a few parking places by the old Coast Guard station (now owned by the town), a fence to lock bikes, and a narrow path to the beach.
The smoothest, widest sand is at the northern limit of the beach along the inlet to New Harbor by the former Coast Guard station.
Many people come to Coast Guard beach by inflatable boat, bringing their beach chairs, umbrellas and picnics with them.
Coast Guard Beach
At the northern end of Charleston Beach, this fine sand beach borders the inlet to New Harbor next to the decommissioned Coast Guard station.
Reached by West Beach Road off Corn Hill Road in the north of the island, this beach was once the town dump, though it's been mostly cleaned up. Now it leads to a modern transfer station (waste processing facility), a walking trail, and the stony beach.
The unpaved access road is often busy with residents driving their trash to the transfer station, which makes it dusty and unpleasant for biking, although it's not a long ride.
There's very little parking space for cars at the end of the road, and no bike rack.
Nature Walk to North Lighthouse
Those wanting a fine long (3.5-mile/5.6-km, 1.5-hour) nature walk start from the southwestern end of West Beach Road and follow the trail north along the beach skirting the Block Island National Wildlife Refuge to North Lighthouse and Settlers' Rock near the northern tip of Block Island.
Nature walk to North Light Interpretive Center (lighthouse), Block Island RI
To get to Block Island's beaches, to get your exercise, and to explore the natural beauty of the island, a bicycle tour is the best way, although mopeds are also available if you'd rather not pedal. In your bicycle wanderings around the island, you should stop at Southeast Light for a glimpse of Block Island history.
Block Island is small enough—only 7 miles (11 km) long (map)—that you can see most of it on a bike tour in one day, and even more enjoyably in two or more days.
Although there are few bike paths, Block Island's roads are lightly trafficked with cars, and most drivers happily share the road with bikers.
Block Island has varied topography. The highest point on the island is 211 feet (64 meters) above sea level. A few of the hills may seem longish and steep if you are not in moderately good physical condition or are not an experienced bicycler, but there's no rush! You can rest. You can walk your bike for a little while.
Bring Your Bike!
It costs only a few dollars to bring your own bike to Block Island on the ferry from Port Galilee.
Rent a Bike on Block Island
Numerous shops rent bicycles and mopeds (motor scooters) on Block Island.
If you rent, most rental shops provide bike locks, but may not provide helmets, so bring your own. You really should wear a helmet when biking, especially on unfamiliar roads.
Bike vs Moped
Bicycles can go anywhere on Block Island. Mopeds are limited to paved roads. Some of Block Island's beaches are reached by unpaved roads. More...
Whether you ride a bicycle or a moped, remember to use sunblock on your hands (particularly the backs), feet (especially the tops), legs, arms, neck and any other exposed areas. People not used to riding in bright sun often overlook the fact that the backs of hands and the tops of feet may be exposed to direct sun for long periods while riding, and painful sunburn may result.
Best Block Island Bike Routes
You could bike all over Block Island in one day if you wanted, but why rush? Various round-trip and loop rides can show you all of the island at your leisure.
Northern Island Bike Route
I'd suggest that your first bike ride be north from Old Harbor to Settlers' Rock and North Light, 4 miles (6.5 km) one-way, 8 miles (13 km) round-trip if you make no detours. At an average speed of 10 to 12 miles per hour, the entire round-trip ride takes less than an hour, although you'll want to stop to see the sights, walk the nature trails, take a swim, etc.
Ride out of Old Harbor along Water Street and Dodge Street, then turn right on Corn Neck Road, which will take you all the way to the northern tip of the island (map).
Along the way you'll pass Fred Benson Town Beach, the best swimming and sunning spot and the only beach with full facilities. It's just off the road, easy of access, with a bike rack.
Three miles (5 km) north of Old Harbor, on the right (east) off Corn Neck Road is a marker for the Clay Head Nature Trail. Ride 0.4 miles (644 meters) along a unpaved, stabilized road to the trailhead parking area. Lock your bike to the bike rack and walk 0.3 mile (500 meters, 10 minutes) along the nature trail to the rock-strewn beach framed by the high sandy cliffs of Clay Head. The surf can be strong here, and there are no facilities (and no lifeguard), but it's a beautiful spot to spend a few minutes.
North of the Clay Head road and nature trail is a network of walking trails on private land known as the Maze.
Back on your bike, continue the final mile to the north tip of the island and Settlers' Rock, where the paved road ends in a parking area and bike rack. The Settlers' Rock monument, erected in 1911, marks the spot where the island's first English settlers landed in 1661, and bears the names of the first male inhabitants. (Uh, we assume there were women as well....)
If you like, lock your bike to the rack opposite the monument and walk the half-mile (800 meters) along the sandy shore of Cow Cove through the seagull-thronged Block Island National Wildlife Refuge to Sandy Point and the North Light. The granite lighthouse dates from 1867 and is now open ($3) Thursday through Monday from 10 am to 4 pm, weather permitting, as an Interpretive Center.
Old Harbor to New Harbor
It's short (10 to 15 minutes one-way), easy and interesting: ride out of Old Harbor along Water Street and Dodge Street to Ocean Avenue, and follow this for 1.3 miles (2 km) all the way to New Harbor (10 to 15 minutes).
At New Harbor, enjoy the view of the Great Salt Pond and perhaps a drink, snack or meal at a restaurant.
Southern Island Loops
The southern part of Block Island presents more bike route choices: you can go for a mile or two, you can make a 10-mile (16-km), 60- to 90-minute loop of the entire southern half of the island, or you can ride part of the big loop then cut across the island eastward back to Old Harbor to shorten your outing.
Southeast Lighthouse & Mohegan Bluffs
A suitable Block Islandish goal for your first southern bike trip is the Southeast Lighthouse about 1.5 miles (2.25 km) due south of Old Harbor.
Spring Street changes names to become Southeast Light Road and Mohegan Trail, which traces the heights of Mohegan Bluffs.
Southeast Light, just off Spring Street (map), sat at the edge of the bluff for decades.
Erosion of the bluffs brought it perilously close to tumbling into the sea. A grass-roots Block Island residents' effort saved it, moving it farther back from the precipice.
Though decommissioned, it is still a beloved landmark, now open to visitors who can walk on its grounds and see its small museum and shop for free, and take guided tours of its tower for a small fee.
Southeast Lighthouse is only one of many New England lighthouses that have been threatened by erosion and higher seas due to climate change. Sankaty Light on Nantucket also had to be moved due to cliff erosion.
For top- and bottom (sea-level) views of the bluffs, stop at Payne's Overlook, have an overlook, the descend the 150 stairs to the beach for a view from the bottom of the bluffs.
From Mohegan Bluffs you can loop back to Old Harbor on Pilot Hill Road (no mopeds allowed) and High Street, a 3.4-mile (5.5-km) loop taking 25 to 35 minutes.
Big Southern Loop
Want to loop all around the southern part of the island? From Southeast Lighthouse and Mohegan Bluffs, keep heading west along Mohegan Trail.
Down the hill to the west of Southeast Lighthouse, if you want some beach time, turn left (south) to reach Snake Hollow. Leave your bike at the head of the tortuous path and walk down to Vail Beach.
Back on the main road, you can turn north on paved Lakeside Drive, or continue westward then northward along unpaved Black Rock Road. Between these two routes is Rodman's Hollow, a large forested glacial ravine now protected as a wildlife refuge. Hiking trails wind through the reservation with trailheads on Black Rock Road and Cooneymus Road.
Lakeside Drive to Old Harbor
If you're not interested in riding the entire Big Southern Loop, continue north along Lakeside Drive, Center Road and Old Town Road back to Old Harbor, making your trip a 6-mile (10-km) loop in about an hour.
West Side Loop
To ride more, from Lakeside Drive turn left (west) at Cooneymus Road, then right (north) on West Side Road. (Cooneymus Road continues straight west to Cooneymus Beach.)
Less than a mile north along West Side Road, an unpaved road on the left, Dorry's Beach Road, goes over a steep but short hill to the sea at Dorry's Beach.
A few minutes farther along, the unpaved Beacon Hill Road goes off to the right (east) and can take you back to Old Harbor via Old Town Road past the Block Island Airport if you've had enough riding for the day.
Otherwise, continue north on the Northwest Loop: along West Side Road past Grace's Cove Road on the left (north) to Grace's Cove Beach, and Champlin Road (unpaved) to Charleston Beach and the old Coast Guard Station at the cut on Harbor Neck.
West Side Road then continues eastward to Ocean Avenue. Turn left on Ocean Avenue for New Harbor, or right for Old Harbor.
Several marinas on the island have fishing boats for hire, and surfcasting for striped bass, bluefish and other delicacies is popular.
Even if you're alone, the marina staff may be able to get together a party to go out, thereby reducing your costs greatly.
For details, drop by any one of the marinas. All the boat-rental and sport-fishing businesses operate out of New Harbor.