We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Long Island In Early October

Canada
Level Contributor
233 posts
23 reviews
Long Island In Early October

I am visiting a friend in New York City and plan to take 3 days to drive around Long Island. I plan to do the following:

Day 1- North Shore- drive down HWY495 and turn at Jericho onto HWY106 north and visit Sagamore Hill, Vanderbilt Museum, Planting Fields Aboretum, stroll around Cold Spring Harbour, Mill Neck and Locust Valley.

Overnight stay at the Hampton Inn at Westbury. I like B&B's but the nice ones are very expensive, and since my group of 3 will just be sleeping, Hampton Inn seems to have good reviews ( noisy near highway?) and we can cancel with little notice in case the weather is bad and we cancel the trip.

Day 2- Drive to Long Beach, then back to mainland and then take the ferry to Fire Island. Then maybe visit Eastport and Hampton Bays if we have time.

Overnight at the Hyatt Hotel at Riverhead.

Day 3- Drive to South Fork all the way to Montauk, then to Shelter Island and ferry to North Fork. We are not wine drinkers, but we like to see the country side.

Day 3 night at Hyatt at Riverhead again,

Day 4- drive back to New York City.

I would appreciate your comments as to :

1)whether the trip makes sense as I cannot estimate driving time due to the traffic condition and along small side roads

2)will Fire Island and Montauk be too cold and windy to visit in the first week of October? Will restaurants be closed on Fire Island?

3) should we see the South Fiork only on Day 3 and stay on Monauk or Shelter Island on night of Day 3 instead of making it back to Riverhead, and then on Day 4, drive along the North Fork and then back to New York City?

Thank you for you r help :-)

53 replies to this topic
long island, ny
Level Contributor
3,052 posts
18 reviews
1. Re: Long Island In Early October

Wow! This is a lot to process! I think I may need a day or 2...LOL

The weather can be beautiful or it can be nasty...won't know until the time comes. We have been swimming in Montauk on Columbus Day weekend which is the second weekend in Oct.

I think my biggest problem is day 2.

Is there a specific reason to go to Long Beach?

I would skip it and hit Jones Beach. Walk the boardwalk.

Drive down Ocean Pkwy to Robert Moses Beach.

Park at field 5 and walk to the Fire Island Lighthouse.

This will be much cheaper and less time consuming than actually going to Fire Island by Ferry.

Then make your way to Riverhead to stay the night.

Day3:

I would explore the south fork and shelter Island and either stay the night in Greenport or stay in the Montauk area and make your way to the North fork in the morning. all of the farm stands and pumpkin picking will be in full swing!

Day 4:

Make your way back to the city.

there is a small Aquarium in Riverhead...Atlantis...you seem to be interested in the water. They do have a 90 minute boat ride that was very fun and informative. If the times are convenient, I highly recommend it.

longislandaquarium.com/adventures-tourboat-i…

This are my first thoughts...and will probably have more...LOL

I'm sure others will have additional ideas!

Canada
Level Contributor
233 posts
23 reviews
2. Re: Long Island In Early October

Thank you Shoney :-)

Really appreciate your reply. I was under the impression I should be spending a great part of Day 2 walking along Fire Island. From your input, sounds like I just need a peek at it from the Lighthouse. Wonder why my guide book highly recommend it, is it because it is a fun place in the summer and not the fall?

I am very interested in history and architecture, what are towns on Long Island you recommend I must not miss? I am concerned that other than the museums, cute towns with the fancy stores, I will be driving along sand dune or rocky beaches and not see a house because they are so exclusive.

Yes, I am a water person, I will check out the boar ride for sure! Thanks for the idea.

I will follow all your suggestions in your reply above.

Thank you very much for all your help :-)

Canada
Level Contributor
233 posts
23 reviews
3. Re: Long Island In Early October

I meant going on the boat ride you suggested , not a "boar ride" LOL

New York City, New...
Destination Expert
for New York City
Level Contributor
97,417 posts
12 reviews
4. Re: Long Island In Early October

I think day 2 is a waste of time in Oct. i also think staying in RIverhead for the plans you have makes no sense. I'd stay in Hampton Bays on night 2 and explore the Hamptons. If you want to go all the way to Montauk, consider staying there for night 3 or, here's a special I noticed if you stay on Shelter Island that might work.

groupon.com/deals/ga-la-maison-blanche-hotel…

Canada
Level Contributor
233 posts
23 reviews
5. Re: Long Island In Early October

Thank you nywhiz, I will rethink Day 2. I have never used groupon before, I will definitely consider that option.

Appreciate your input.

Edited: 18 August 2012, 00:26
New York City, New...
Destination Expert
for New York City
Level Contributor
97,417 posts
12 reviews
6. Re: Long Island In Early October

I found the offer on travel-ticker.com although it does come from groupon. I've not stayed at that inn but have had brunch there. It seems very nice and is quite close to the beach but Shelter Island will definitely be quiet at that time with a lot of things closed. Staying in the Hamptons, Sag harbor or Montauk would have more action but this is a good deal. Just keep in mind you need to take the ferry to/from Shelter Island.

It's just that Riverhead is really too far to drive to go as far as Montauk. The map must make it look very close but with only one road in and out it's not.

You don't say what days of the week you're doing this but I'll warn we have a long weekend called Columbus day that falls early this year on Oct 5-8. Traffic on that weekend is mad and the driving in the Hamptons,the Morth Fork and everywherereally is awful. A lot of people with kids go out to LI for pumpkin patches, apple picking etc.

New York
Level Contributor
9 posts
6 reviews
7. Re: Long Island In Early October

I live on Long Island. I was thinking that after Cold Spring Harbor, you might want to check out Port Jefferson. You could stay at Danford's Inn there. It's such a cute, quirky town with lovely stores and restaurants. A New England feel. Feel free to PM me with questions.

Canada
Level Contributor
233 posts
23 reviews
8. Re: Long Island In Early October

Thank you very much nywhiz and Jackaroo26 :-)

I will be going to Long Island on Oct 8, after the mad weekend.

Should I bother with Jones Beach on Day 2 if most of what I planned for Day 2 is not a good idea for October?

One option is to stay at Port Jefferson night of Day 1 and drive to the Hamptons and stay there night of Day 2 , then see Montauk, Shelter Island and the North Fork on Day 3 and stay at Riverhead night of Day 3 and back to New York city on Day 4 morning. There is no reason why I must stay at Riverhead other that it is after the North Fork tour and I know the Hyatt has good prices. I am open to more suggestions. I am not interested in winery tours as I am not a big wine drinker.

Thank you Jackaroo26 for offering to answer more questions via PM.

Thank you!

New York City, New...
Destination Expert
for New York City
Level Contributor
97,417 posts
12 reviews
9. Re: Long Island In Early October

I wouldn't bother with Jones Beach or Fire Island in Oct. Not to say the beaches aren't nice, but it won't likely be sitting on the beach weather then, and even if it is, the beaches further east are just as nice (imo) and don't require ferries as Fire Island would. While you say in a later post you're interested in architecture and history, I see a lot of time being taken up by shoreline views and water. ?

Yes, staying in Port Jeff is an option for day 1 and more charming than the Hampton Inn in Westbury but

>I don't think you will be able to see everything you list for day 1 all in one day. If you go to Port Jeff. you're further away. If you stay in Westbury/Garden City/Carle Place area, you can see what you missed on day 1 easily if you want. What about Old Westbury Gardens, btw?? Gorgeous mansion and gardens that should be open to the public.

http://www.oldwestburygardens.org/

> Who's in your group? (ie kids? all adults? men/women?) Danfords only has rooms with 2 doubles. If you're 3 adults, I think one of the chains in Westbury/Garden City/Carle Place will likely have 2 queens.

I think you really have to decide what exactly you want to see first and then pick places to stay. I continue to believe staying in Riverhead is a mistake. If it's all about budget, there are places to stay in Hampton Bays that would be more affordable that would at least get you closer to the Hamptons OR stay out in Montauk for a night.

New York City, New...
Destination Expert
for New York City
Level Contributor
97,417 posts
12 reviews
10. Re: Long Island In Early October

North Fork tour?

Get answers to your questions about Shelter Island