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06 Sep 2025

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10 Best Places for Weekend Trips From Hempstead, NY

Weekend Getaway Itinerary Overview from Hempstead, NY

Embark on a memorable journey with our curated selection of the top 10 weekend destinations near Hempstead, NY. Start your adventure by unwinding on the picturesque shores of Montauk, exploring the glamorous villages and stunning beaches of The Hamptons, or reveling in the laid-back charm of Fire Island's unique, car-free environment. Nature lovers can hike scenic trails and enjoy panoramic vistas at Bear Mountain State Park or discover the immersive art installations at Storm King Art Center. Dive into culture and history with a visit to Philadelphia, PA, known for its iconic landmarks and vibrant food scene, or stroll through the cultural treasures of New Haven, CT, home to Yale University. Artistic souls will be captivated by Beacon’s galleries and Dia:Beacon, while Hudson, NY invites you with its antique shops and historic streets. Conclude your trip in Mystic, CT, where maritime history and aquarium adventures await. Each location offers a unique experience, perfect for unwinding and making unforgettable memories close to home.

Recommended Activities

1
Montauk
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Montauk offers beautiful beaches, scenic lighthouse views, fresh seafood, and a relaxed coastal atmosphere perfect for a peaceful weekend retreat.
2
The Hamptons
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The Hamptons are famous for charming villages, stunning beaches, upscale restaurants, and a vibrant arts scene, making it ideal for a luxurious and memorable getaway.
3
Fire Island
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Fire Island is known for its pristine sandy beaches, unique car-free communities, picturesque boardwalks, and opportunities for outdoor activities like biking and wildlife watching.
4
Bear Mountain State Park
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Bear Mountain State Park is ideal for hiking, picnicking, and enjoying breathtaking views of the Hudson River, with attractions like a zoo, lake, and historic inn for a perfect nature escape.
5
Philadelphia, PA
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Philadelphia offers rich American history, famous landmarks like the Liberty Bell and Independence Hall, renowned museums, and vibrant food markets for a culturally enriching weekend.
6
New Haven, CT
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New Haven is home to Yale University, with beautiful campus architecture, world-class museums, lively eateries, and a burgeoning arts and music scene, making it a diverse urban getaway.
7
Beacon, NY
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Beacon is known for its vibrant arts community, the renowned Dia:Beacon contemporary art museum, scenic hiking trails, and charming Main Street filled with shops, galleries, and cafes.
8
Storm King Art Center
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Storm King Art Center offers a unique outdoor experience with massive contemporary sculptures set in a sprawling landscape, perfect for art lovers and nature enthusiasts alike.
9
Hudson, NY
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Hudson features a lively downtown with antique shops, farm-to-table restaurants, historic architecture, and a thriving arts and music scene, making it a trendy and relaxing destination.
10
Mystic, CT
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Mystic is famous for its historic seaport, charming downtown, beautiful waterfront, engaging maritime museums, and family-friendly attractions like the Mystic Aquarium, making it an ideal spot for both relaxation and exploration.

Restaurants

The Lobster Roll (LUNCH)
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4.5
$$$$
The Lobster Roll (LUNCH)
This iconic roadside eatery in Amagansett serves up classic lobster rolls and retro vibes, making it a must-stop for a genuine Hamptons experience.
4.5
$$$$
Mystic Pizza, Mystic, CT
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4.4
$$$$
Mystic Pizza, Mystic, CT
Made famous by the 1988 movie, this pizzeria in Mystic, CT offers delicious pies and a nostalgic atmosphere for movie buffs and foodies alike.
4.4
$$$$
The Pandorica
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4.4
$$$$
The Pandorica
A Doctor Who-themed eatery in Beacon, NY with a quirky menu and décor, perfect for sci-fi fans seeking a unique and immersive dining experience.
4.4
$$$$
Terrain Garden Café
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4.4
$$$$
Terrain Garden Café
Located in Westport, CT, this charming café is set within a garden and lifestyle shop, offering farm-to-table dishes in a truly enchanting setting.
4.4
$$$$
The Cave Mountain Brewing Company
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4.6
The Cave Mountain Brewing Company
Set in the Catskills near Hudson, NY, this brewery offers creative pub fare and craft beers in a cozy, rustic hideaway that feels worlds away from the city.
4.6

Hotels

The Surf Lodge
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3.9
The Surf Lodge
An iconic Montauk hotel known for its laid-back beach atmosphere, live music, and stylish bohemian décor, perfect for a memorable coastal stay.
3.9
Winvian Farm
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4.6
Winvian Farm
Located in the Litchfield Hills, CT, this luxury resort offers themed cottages including a treehouse and a restored helicopter suite, making each stay unique and adventurous.
4.6
The Dan'l Webster Inn & Spa
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4.4
The Dan'l Webster Inn & Spa
A historic inn in Sandwich, MA with uniquely decorated rooms, beautiful gardens, and a blend of colonial charm and modern luxury amenities.
4.4
The Roundhouse
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8.3
$$$$
The Roundhouse
A boutique hotel in Beacon, NY with rooms overlooking waterfalls and modern, industrial-chic design, offering a romantic and scenic atmosphere.
8.3
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The Inn at Stony Creek
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4.9
The Inn at Stony Creek
A quaint B&B in Warwick, NY surrounded by nature, featuring themed rooms and personalized touches for an intimate, countryside escape.
4.9

Local Events & Happenings

Voyage - Celebrating The Music of Journey
Voyage - Celebrating The Music of Journey
The event will take place at Martire Family Arena in Fairfield.
Martire Family Arena in Fairfield (4.16 mi)
28 Sep 2025
Visit Website
Sacred Heart v Delaware State Tailgate Village
Sacred Heart v Delaware State Tailgate Village
The event will take place at Campus Field in Fairfield.
Campus Field in Fairfield (4.56 mi)
27 Sep 2025
Visit Website

Sacred Heart v Howard Tailgate Village
Sacred Heart v Howard Tailgate Village
The event will take place at Campus Field in Fairfield.
Campus Field in Fairfield (4.56 mi)
11 Oct 2025
Visit Website
Sacred Heart v New Haven Tailgate Village
Sacred Heart v New Haven Tailgate Village
The event will take place at Campus Field in Fairfield.
Campus Field in Fairfield (4.56 mi)
1 Nov 2025
Visit Website
Sacred Heart v Virginia Lynchburg Tailgate Village
Sacred Heart v Virginia Lynchburg Tailgate Village
The event will take place at Campus Field in Fairfield.
Campus Field in Fairfield (4.56 mi)
8 Nov 2025
Visit Website
Sacred Heart v Merrimack Tailgate Village
Sacred Heart v Merrimack Tailgate Village
The event will take place at Campus Field in Fairfield.
Campus Field in Fairfield (4.56 mi)
15 Nov 2025
Visit Website
SHU Park Ave Club v Manhattanville
SHU Park Ave Club v Manhattanville
The event will take place at William H. Pitt Center in Fairfield.
William H. Pitt Center in Fairfield (4.62 mi)
29 Dec 2024
Visit Website

Travel Gems from Reddit

30 votes, 47 comments. I was just wondering if there's a good day trip anyone would recommend for the upcoming month. I know its winter and so the
Any daytrip from NYC to Long Island (no car) that you would Recommend?
30 votes, 47 comments. I was just wondering if there's a good day trip anyone would recommend for the upcoming month. I know its winter and so the
/r/longisland
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12 votes, 31 comments. Thoughts on which of these may be our best bet for a weekend getaway late summer? Were looking for a cute downtown and then
NY weekend getaway?
12 votes, 31 comments. Thoughts on which of these may be our best bet for a weekend getaway late summer? Were looking for a cute downtown and then
/r/upstate_new_york
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26 votes, 103 comments. Looking to get away in the next few weeks with the wife. Ideally a nice Bed & Bfast or a small Resort. Have been looking into
Whats your recommendation for a weekend getaway that is 2-3 hours away from NYC?
26 votes, 103 comments. Looking to get away in the next few weeks with the wife. Ideally a nice Bed & Bfast or a small Resort. Have been looking into
/r/hudsonvalley
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35 votes, 45 comments. Im totally unfamiliar with upstate NY but would really love to plan a weekend trip there over the summer. My husband and I
Weekend getaway with a walkable city?
35 votes, 45 comments. Im totally unfamiliar with upstate NY but would really love to plan a weekend trip there over the summer. My husband and I
/r/upstate_new_york
View on Reddit
Fun weekend trips with kids from Westchester Cute towns to visit in Hudson Valley Quick family getaways near Westchester New to Reddit? Create your account and connect with a ...
Any suggestions for a local (<3 hr. drive from southern ...
Fun weekend trips with kids from Westchester Cute towns to visit in Hudson Valley Quick family getaways near Westchester New to Reddit? Create your account and connect with a ...
/r/Westchester
View on Reddit

Music for Your Journey

Red Hot Chili Peppers - Road Trippin'
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Red Hot Chili Peppers - Road Trippin'
A mellow, reflective tune perfect for setting a relaxed vibe at the start of your journey.
Fleetwood Mac - Go Your Own Way - 2004 Remaster
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Fleetwood Mac - Go Your Own Way - 2004 Remaster
An energetic classic rock track that captures the excitement of exploring new destinations.
Katrina & The Waves - Walking On Sunshine
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Katrina & The Waves - Walking On Sunshine
An upbeat, feel-good song that's sure to boost your mood as you hit the road.

Rusted Root - Send Me on My Way
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Rusted Root - Send Me on My Way
A joyous anthem full of wanderlust, perfect for cruising towards adventure.
Edward Sharpe & The Magnetic Zeros - Home
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Edward Sharpe & The Magnetic Zeros - Home
This heartfelt track celebrates the concept of home and the joy of returning after a journey.
Rihanna - Shut Up And Drive
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Rihanna - Shut Up And Drive
A fun, high-energy pop song ideal for long stretches of open road.
Rascal Flatts - Life is a Highway
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Rascal Flatts - Life is a Highway
A road trip anthem that brings energy and excitement to any travel playlist.
The Beatles - Here Comes The Sun - Remastered 2009
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The Beatles - Here Comes The Sun - Remastered 2009
A timeless classic that uplifts and inspires as you travel to beautiful destinations.
Willie Nelson - On The Road Again - Live
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Willie Nelson - On The Road Again - Live
A carefree country tune that celebrates the freedom and joy of travel.
Shoreline Mafia - ROCKIN
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Shoreline Mafia - ROCKIN
A dreamy, melodic piece that's perfect as you approach scenic coastlines.

Your Trips Will Appear Here

10 Best Places for Weekend Trips From Hempstead, NY

Weekend Getaway Itinerary Overview from Hempstead, NY

Recommended Activities

Montauk

The Hamptons

Fire Island

Bear Mountain State Park

Philadelphia, PA

New Haven, CT

Beacon, NY

Storm King Art Center

Hudson, NY

Mystic, CT

Restaurants

The Lobster Roll (LUNCH)

The Lobster Roll (LUNCH)

Mystic Pizza, Mystic, CT

Mystic Pizza, Mystic, CT

The Pandorica

The Pandorica

Terrain Garden Café

Terrain Garden Café

The Cave Mountain Brewing Company

The Cave Mountain Brewing Company

Hotels

The Surf Lodge

The Surf Lodge

Winvian Farm

Winvian Farm

The Dan'l Webster Inn & Spa

The Dan'l Webster Inn & Spa

The Roundhouse

The Roundhouse

The Inn at Stony Creek

The Inn at Stony Creek

Local Events & Happenings

Voyage - Celebrating The Music of Journey

Voyage - Celebrating The Music of Journey

Sacred Heart v Delaware State Tailgate Village

Sacred Heart v Delaware State Tailgate Village

Sacred Heart v Howard Tailgate Village

Sacred Heart v Howard Tailgate Village

Sacred Heart v New Haven Tailgate Village

Sacred Heart v New Haven Tailgate Village

Sacred Heart v Virginia Lynchburg Tailgate Village

Sacred Heart v Virginia Lynchburg Tailgate Village

Sacred Heart v Merrimack Tailgate Village

Sacred Heart v Merrimack Tailgate Village

SHU Park Ave Club v Manhattanville

SHU Park Ave Club v Manhattanville

Travel Gems from Reddit

Any daytrip from NYC to Long Island (no car) that you would Recommend?

NY weekend getaway?

Whats your recommendation for a weekend getaway that is 2-3 hours away from NYC?

Weekend getaway with a walkable city?

Any suggestions for a local (<3 hr. drive from southern ...

Music for Your Journey

Red Hot Chili Peppers - Road Trippin'

Red Hot Chili Peppers - Road Trippin'

Fleetwood Mac - Go Your Own Way - 2004 Remaster

Fleetwood Mac - Go Your Own Way - 2004 Remaster

Katrina & The Waves - Walking On Sunshine

Katrina & The Waves - Walking On Sunshine

Rusted Root - Send Me on My Way

Rusted Root - Send Me on My Way

Edward Sharpe & The Magnetic Zeros - Home

Edward Sharpe & The Magnetic Zeros - Home

Rihanna - Shut Up And Drive

Rihanna - Shut Up And Drive

Rascal Flatts - Life is a Highway

Rascal Flatts - Life is a Highway

The Beatles - Here Comes The Sun - Remastered 2009

The Beatles - Here Comes The Sun - Remastered 2009

Willie Nelson - On The Road Again - Live

Willie Nelson - On The Road Again - Live

Shoreline Mafia - ROCKIN

Shoreline Mafia - ROCKIN