Looking for a relaxed suburban escape with beaches, parks, and history? Head to Smithtown! Located on Long Island’s scenic North Shore, Smithtown offers charming downtown shops, beautiful nature preserves, and easy access to Long Island’s beaches. Whether you’re into hiking, boutique shopping, or waterfront dining, Smithtown serves up a perfect mix of small-town charm and coastal adventure.

Best Time to Visit

The best time to visit Smithtown is during late spring through early fall (May–October). Warm weather makes it ideal for beach outings, hiking, and enjoying outdoor festivals and farmers markets.

How to Get There

  • If you are traveling by car: Smithtown is accessible via the Long Island Expressway (I-495) and the Northern State Parkway, about 1.5 hours east of New York City (depending on traffic).
  • By Train: Take the Long Island Rail Road (LIRR) Port Jefferson Branch to Smithtown Station for convenient access from NYC and other Long Island communities.
  • By Plane: Long Island MacArthur Airport (ISP) is about 25 minutes away; JFK and LaGuardia Airports are about 1–1.5 hours away by car.

Where to Stay

  • Americas Best Value Inn Smithtown/Long Island – Budget-friendly option close to downtown and major attractions.
  • Hyatt Regency Long Island – Upscale hotel located nearby in Hauppauge with a golf course, pool, and modern amenities.
  • Charming Long Island B&Bs – Stay at cozy bed-and-breakfasts in neighboring villages like Stony Brook or Port Jefferson for a more personal experience.

Best Things to Do

Read, Learn, and Connect: Discover Endless Resources at Smithtown Library

Read, Learn, and Connect: Discover Endless Resources at Smithtown Library

© Smithtown Library

The Smithtown Library on Long Island can trace its start back to the year 1907 when several materials were housed inside the law office of Judge Lawrence Smith. This collection was moed between 1909 to 1912 to a different small building before moving to Smithtown’s Epenetus Smith Tavern. The first of the library’s permanent buildings opened in August of 1912 and was moved later in 1950 to its present day location. The Smithtown Library, which hosts events as well, is now made up of four separate buildings, which are located in Nesconset, Kings Park, and Commack, in addition to Smithtown.

Smithtown, NY, Phone: 631-360-2480

Escape into Nature: If You Crave Peaceful Trails, Then Explore Caleb Smith State Park

Escape into Nature: If You Crave Peaceful Trails, Then Explore Caleb Smith State Park

© Caleb Smith State Park

Caleb Smith State Park is a state preserve within Suffolk County’s Smithtown, located near Long Island’s northern shore. The park has changed named since it was established, formerly known as Nissequogue River State Park, and Wyandanch Preserve before that. The Caleb Smith State Park encompasses a total of 548 acres and is primarily managed as one of the state’s nature preserves, but also offers opportunities for outdoor recreation activities, such as cross-country skiing, fishing, and hiking. Recreation programs are offered as well, including a nature trail and a nature museum home to a number of wildlife displays.

581 W Jericho Turnpike, Smithtown, NY 11787, Phone: 631-265-1054

Activities and Attractions for Couples:

Applaud Local Talent: Catch a Live Show at Smithtown Center for the Performing Arts

Applaud Local Talent: Catch a Live Show at Smithtown Center for the Performing Arts

© Smithtown Center for the Performing Arts

The Smithtown Center for the Performing Arts first opened its doors in October of 2002 with a mission to bring high-quality professional entertainment to both Smithtown and its surrounding communities, as well as provide educational opportunities to kids living on Long Island. The Smithtown Center for the Performing Arts has held more than 1,500 performances since its beginnings that consist of around eighty different stage presentations. The performing arts center is housed inside the historic Smithtown Theatre, which started performances in the 1940’s operated by the Prudential Circuit. In 1999, local residents banded together to save the theater from destruction.

2 East Main St, Smithtown, NY 11787, Phone: 631-724-3700

Push Your Limits: Train, Move, and Transform at Transfitnation

Push Your Limits: Train, Move, and Transform at Transfitnation

© Transfitnation

Transfitnation in Smithtown, New York is a personal training and lifestyle transformation studio that provides both studio-based and in-home personal training. The personal training and wellness studio in Smithtown was established to help people in town and the surrounding area live fulfilling and healthy lives by making small changes in their lifestyle. The programs and services here are designed to help people overcome obstacles by transforming their health, body, and mind, whether their goal is to improve overall health, eliminate joint pain, get stronger, tone up, or lose weight. Transfitnation specializes in creating exercise experiences that teach how to move and eat better.

20 Gilbert Ave, Smithtown, NY 11787, Phone: 631-974-9491

Craft and Create: Dive Into DIY Fun at AR Workshop

Craft and Create: Dive Into DIY Fun at AR Workshop

© AR Workshop

AR Workshop is a boutique DIY studio with numerous locations across the country, offering hands-on classes in creating charming and custom home decor, all from raw materials. Both local residents and visitors alike in Smithtown, New York can join one of the many instructor-led workshops to make their own customized round signs, frames, wood signs, knit blankets, trays, centerpiece boxes, lazy susans, canvas pillows, and much more. The AR Workshop boutique also features a retail area as well, focused on interior design and styling, which offers trend-setting accessories and decor that often pair well with items made in the workshops.

83 E Main St, Smithtown, NY 11787, Phone: 631-352-0221

Where to Eat:

Savor Authentic Spice: If You Love Bold Flavors, Dine at Raan Thai

Savor Authentic Spice: If You Love Bold Flavors, Dine at Raan Thai

© Raan Thai

Raan Thai Cuisine is a family-owned and operated, award-winning restaurant serving authentic Thai cuisine to the people of Smithtown and the surrounding communities. Natthamon Saengthong, the owner and chef, moved to the United States from a small town in Thailand a couple hours from Bangkok and grew up learning how to cook Thai dishes from her grandmother and mother. Raan Thai opened in April of 2011 featuring a traditional, low-key Thai ambiance with a touch of class. The menu here focuses on traditional Thai cooking techniques and uses several fresh Thai herbs and all sauces are homemade.

203 Terry Rd, Smithtown, NY 11787, Phone: 631-656-5887

Grab a Slice of Tradition: Enjoy Classic Italian Favorites at Monte’s Pizzeria

Grab a Slice of Tradition: Enjoy Classic Italian Favorites at Monte’s Pizzeria

© matttilda/stock.adobe.com

Monte’s Pizzeria is a one-of-a-kind pizzeria in Smithtown, New York as it doesn’t use Trans Fat to make their food, everything is prepared using 100-percent soy oil, offering a healthier option for delicious food. Along with both specialty and traditional pizzas, the extensive menu at Monte’s Pizzeria also includes salads, appetizers, entrees, pasta, paninis, and wraps. The wide selection of pies include classic staples like the Sicilian and the Neopolitan to creative favorites, such as the Artichoke Spinach Dip Pizza and the Full Monte, which features every topping available at the pizzeria with the exception of anchovies.

300 Maple Ave, Smithtown, NY 11787, Phone: 631-979-2020

Must-see if you are a first-time visitor:

  • Relax at Sunken Meadow State Park – Swim, hike, picnic, or bike along the boardwalk with panoramic views of Long Island Sound.
  • Tour the Smithtown Historical Society Grounds – Step back into colonial times with preserved historic homes, barns, and community events.
  • Explore downtown Smithtown – Browse local boutiques, cafés, and restaurants along Main Street and around town.
  • See the Whisper the Bull Statue – Snap a photo with this iconic Smithtown landmark commemorating the town's founding legend.

Where to Eat

  • Maureen’s Kitchen – Legendary breakfast and brunch spot known for massive portions and creative specials (cash only, often a wait but worth it).
  • H20 Seafood & Sushi – Upscale dining featuring fresh seafood, sushi, and contemporary American dishes in a stylish setting.
  • Insignia Prime Steak & Sushi – Sleek, modern steakhouse offering premium cuts, sushi, and an extensive wine list just outside of Smithtown.

If you are interested in local events:

  • Smithtown Festival Day (June) – Family-friendly street festival with vendors, food trucks, live entertainment, and activities downtown.
  • Smithtown Historical Society’s Heritage Ball (Fall) – Elegant fundraising event celebrating local history with dining, auctions, and dancing.
  • Summer Concerts at Hoyt Farm (Summer) – Free outdoor concerts, kids’ activities, and food vendors in a beautiful park setting.

If you are looking for unique day trips within 30 Minutes of Smithtown, New York:

  • Stony Brook Village (20–25 min) – Quaint New England-style village with shopping, dining, and waterfront views along the harbor.
  • Port Jefferson, NY (20–25 min) – Stroll the lively harborfront, shop downtown boutiques, and enjoy waterfront dining.
  • Bayard Cutting Arboretum State Park (25–30 min) – Explore stunning gardens, riverfront trails, and peaceful landscapes.
  • Fire Island National Seashore (via Sayville) (30 min to ferry) – Catch a ferry to pristine beaches, coastal trails, and historic lighthouses.
  • Caumsett State Historic Park Preserve (30 min) – Hike, bike, or horseback ride through expansive meadows and along the Long Island Sound coast.

Frequently Asked Questions:

  • Where is Smithtown, New York located?
    • Settled first during the 1600s, Smithtown, New York, is a town situated on Long Island.
  • How did Smithtown get its name?
    • Its name came from a local legend, which says that after a settler named Richard Smith rescued the daughter of a Native American chief, he was given all of the land he could circle on a bull in a single day.
  • What is the legend behind Smithtown’s land acquisition?
    • According to legend, Richard Smith picked the year’s longest day to ride the bull and acquired what is now known as Smithtown.
  • What activities are available in Smithtown today?
    • The town today offers numerous things to do for both visitors and locals alike.

Plan Your Trip