Southold Travel Guide

Plan your trip to Southold, NY with this detailed travel guide, covering everything from must-visit places and activities to food and drink scene, safety tips, and transportation options.


A Comprehensive Travel Guide to Southold, New York

Located in Suffolk County, Long Island, Southold is a charming town that offers a perfect mix of natural beauty, rich culture, and fascinating history. This travel guide is designed to help you plan the perfect trip to Southold, covering everything from must-visit places and activities to food and drink scene, safety tips, and transportation options.

Introduction to Southold

Southold is a quaint town that is known for its vibrant cultural scene, stunning landscapes, and breathtaking beaches. The town has a rich history that dates back to the arrival of English settlers in the mid-17th century. Today, Southold is a popular vacation destination that attracts millions of visitors from all around the world.

List of Places to Visit in Southold

There are plenty of places to visit in Southold that are sure to leave you mesmerized. Here is a list of the top attractions that you should not miss:

Culturally Important Attractions: Museums and Historical Places

  • Custer Observatory

  • Horton Point Lighthouse and Nautical Museum

  • Southold Historical Society Museum

  • Old House

Natural Attractions of Southold: Outdoor Adventures and Scenic Views

  • Southold Bay Beach

  • Arshamomoque Pond Preserve

  • Orient Beach State Park

  • Shinnecock Bay

Hiking/Biking Routes of Southold

Southold boasts some of the most picturesque hiking and biking trails in the country. Here are a few of the most popular routes:

  • North Fork Trail

  • Hallock State Park Trail

  • Goldsmith Inlet Trail

  • Pine Barrens Trail

Best Things to Do in Southold: Activities and Tours

Southold offers a plethora of activities and tours that are sure to keep you entertained throughout your stay. Here are a few of the best things to do in Southold:

  • Wine Tours

  • Fishing Charters

  • Jet Skiing

  • Golfing

Week-Long Itinerary for Southold

If you are planning to spend a week in Southold, here is a sample itinerary that you can follow:

Day Activity
1 Visit Horton Point Lighthouse and Nautical Museum, Southold Historical Society Museum, and Old House
2 Explore the North Fork Trail and have a picnic at Arshamomoque Pond Preserve
3 Spend a day at Southold Bay Beach
4 Take a wine tour
5 Go fishing or charter a boat for the day
6 Attend a golfing event
7 Take a jet ski excursion in the bay

Food and Drink Scene of Southold

Southold’s food and drink scene is sure to leave you impressed. Here are some of the must-try dishes and local beverages:

Must-Try Dishes

  • Local seafood like Clams, Oysters, and Lobster

  • Corn on the Cob

  • Blue Point oysters

  • Long Island duckling

Local Beverages

  • Wine

  • Tea

  • Coffee

  • Juices

Where to Stay in Southold: Hotels, Hostels, and Guesthouses

Southold offers plenty of accommodation options that cater to a range of budgets. Here are a few of the top hotels, hostels, and guesthouses in the town:

  • Heron Suites

  • The Duncan Inn

  • North Fork Guest House

  • Andrew’s Legacy Bed and Breakfast

What to Buy in Southold: Souvenirs and Local Products to Bring Home

Southold boasts plenty of shops and stores that offer locally made products, handicrafts, and souvenirs. Here are some of the best places to shop in Southold:

  • Kait’s Angels Thrift Store

  • Condzella’s Farm Stand

  • The Farmhouse

Local Culture and Customs of Southold

Southold has a rich culture that is reflected in its historic sites, museums, and galleries. The town is known for its love of nature, art, and history. Visitors are expected to show respect for the town’s culture and customs.

Best Time to Visit Southold

The best time to visit Southold is during the summer months (June to August) when the weather is warm and sunny, and the town is overflowing with tourists and activities.

Do’s and Don’ts of Southold

Do:

  • Take time to explore the town’s historic sites and museums

  • Try the local seafood

  • Attend a wine tour

Don’t:

  • Litter or damage the town’s environment

  • Disrespect the town’s culture and customs

  • Ignore safety regulations while engaging in outdoor activities

Safety and Health

Safety in Southold

Southold is a relatively safe town, with low crime rates. However, visitors are advised to take necessary precautions while exploring the town’s outdoors and beaches.

Health in Southold

Southold has plenty of healthcare facilities, including hospitals, clinics, and pharmacies. Visitors are advised to carry a first-aid kit and seek medical help if needed.

Getting to Southold: Transportation Options and Logistics

Southold is well-connected with other parts of New York via roadways, railways, and airways. Here are some of the best ways to reach Southold:

Airports Near Southold

  • Long Island MacArthur Airport (ISP)

  • John F. Kennedy International Airport (JFK)

  • LaGuardia Airport (LGA)

Bus Stations Near Southold

  • Hampton Jitney

Other Options

  • Hire a Car

  • Take a Taxi

  • Rent a Bicycle

How to Get Around in Southold

Southold is best explored on foot, bike, or car. Visitors can also hire taxis or rent bikes to get around town.

Where to Go Next from Southold: Nearby Destinations and Excursions

Southold’s strategic location makes it easy to explore nearby destinations and excursions. Here are a few places that you can visit:

  • Greenport Village

  • Riverhead

  • Shelter Island

  • Montauk

Conclusion

Southold offers a perfect blend of history, culture, and natural beauty. This comprehensive travel guide is designed to help you plan the perfect trip to Southold, covering everything from must-visit places and activities to food and drink scene, safety tips, and transportation options. So pack your bags, and get set to explore Southold like never before.