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WestJet has had an overnight flight nonstop from Winnipeg to Halifax. If you watch their website, and book early enough, the fares are cheap. My wife and I flew return for about $1050 this past July.

I'm originally from the Halifax area and usually get home for a visit once or twice a year.  
 
So many things to do!!!  
 
Depending on your family's interests some things that come to mind are:  
 
Halifax Citadel historic site - Right in the middle of downtown.  
 
On the Waterfront in Halifax you will find lots of options for boat tours of the harbour. With a 9 year old the "Harbour Hopper" would probably be a hit. It's a city tour on an amphibious vehicle that drives around downtown then proceeds right into the water.  
 
The art gallery of Nova Scotia is very cool. They have Maud Lewis' entire house inside one of the galleries. If you haven't heard of her she's worth a google search, quite an amazing story.  
 
You'd have check the dates but sometime in August there is a huge sandcastle competition at Clam Harbour beach just outside of Halifax. Be warned though. It is crazy busy, finding a spot to park will be hard and you will probably have to park a long way away and walk.  
 
Popular ocean beaches near Halifax are Rainbow Haven and Lawerencetown. If it's your first visit to the coast you really need to dip in the ocean at least once!  
 
Another tip, I've noticed in years before the tourist information center at the Riverbank discovery center gets in tourist materials from across Canada. You could check there and pick up this years brochures and materials when they are available. There should be a big one called the "Doers and Dreamers Guide" which is the big one put out by the Nova Scotia Department of tourism. Lots of great info in it.  
 
Hope some of that helps, enjoy your trip!

Definitely check out St.Andrews, New Brunswick. Beautiful town with lots of touristy things to do, including whale watching. Late summer or early fall is by far the best time to go, so August will be perfect.  
P.E.I. is also quite nice.  
If flying from Winnipeg, Air Canada is the only option I believe, at least, flying to Saint John it was the only option. Leave Winnipeg and connect in either Toronto or Montreal.  
Check Expedia.ca for some good info on package deals for hotel, flight, and car rentals.  
 
Edited by ChristopherMacDonald, 2018-12-03 14:11:45

My dad was a maratimer and when he took me the first time as a kid a few things stayed with me for sure!  
1. Anne of Green Gables site in PEI  
2. Hopewell Rocks / Bay of Fundy in NB  
3. Kings Landing historical site in NB  
What a great family trip you’ve planned! You won’t be at a loss for activities or for dining choices, eat all the seafood!! Lol  
Plus you’re going to get to see the new bridge to PEI!  
Hope you have an amazing holiday!

*K* said "Planning a trip in august, we have never flown before so wondering if anyone has tips of when and where to buy the best priced tickets and any recommendations of must things to see & do while there, there will be a 9yr old with us. "

here's a few great places you'd wan to check out in Nova Scotia..https://annapolisvalleyexhibition.com  
the week of Aug 11-17 is the exhibition which is similar to the Brandon summer fair but on a smaller and more fun scale. that's the link above.  
 
The Annapolis valley is absolutely beautiful and has lots of great places to go to, the zoo in Aylesford:,http://www.oaklawnfarmzoo.ca  
 
Port George, Margaretsville, Hampton, Port Lorne all on the Bay of Fundy known as the north mountain.  
 
Check out Pearles's in the town of Paradise on hwy 1 between lawrencetown and closer to Bridgetown there haddie bits and well all their food is delicious and you wont regret it !!  
 
Also along that shore is Annapolis royal where they have Fort Anne, continuing along you can go to Upper Clements park:http://upperclements.com/en/home/upper-clements  
 
Digby is a beautiful waterfront https://www.digby.ca  
 
check out the links and have a fabulous time and enjoy the fresh haddock and seafood!!

I have never been to the maritime's, it's still on my list. One think I really want to go see is the Royal St John's Regatta, it's held 3rd week in July every year.

Where I was born & raised check out this video https://www.mikesroadtrip.com/pei-road-trip-guide