Stuttgart Wine Festival

The Stuttgart Weindorf is a lovely festival. What happens is local wineries and wine taverns close their doors to the public and open up temporary restaurants from the Marktplatz to Schillerplatz. The emphasis is as much on local food as wine, and the atmosphere is traditional and cozy, not fancy and upscale. Most wines served are dry whites and mild reds, as that's what the region specializes in. It's a great time! It's just good to browse and see what looks appealing in terms of food. Do try kaesespaetzle (local version of macaroni and cheese) and maultaschen (local version of ravioli).

There's a lot else to do here, including Germany's best auto museum - the Mercedes-Benz museum, a wonderful historic zoo and botanical garden (the Wilhelma), a well preserved medieval town nearby (Esslingen, 15 minutes by train from Stuttgart) and one of Germany's grandest baroque palaces (Ludwigsburg, 20 minutes ride from Stuttgart.)

As for Legoland, you can take a train fairly easily. For a group your size your best option is to get a Quer-durchs-Land-Ticket or a Schönes-Wochenende-Ticket depending on whether it's a weekday or a weekend for your group. You can purchase it at a DeutscheBahn machine at the train station or in person at the DB Reisenzetrum at the train station. This will give your entire group all-day travel on regional trains. For your trip this means you take the IRE (Inter-Reggio-Express) to Ulm, then transfer to a local train to Gunzburg. From the Gunzburg station, a shuttle will take you to Legoland (schedule here: https://endpoint913813.azureedge.net/globalassets/pdf/uvid-49602f/818a_hauptsaison_2017.pdf)

The Legoland shuttle apparently also goes from Ulm, so you could pick it up there as well.

What you have to be careful of with these special train tickets is NOT taking an IC, EC, or ICE train (intercity, eurocity, or intercity express respectively). These are not regional trains and are not included in the ticket. However the difference between the regional trains and the fast trains for this particular trip is not worth the excessive cost of buying fast tickets for your group. (Less than 30 minutes difference).

I hope that helps and let me know if you have any other questions!

Sarah,
Thank you for your assistance with both the Stuttgart Wine Festival (wow food and wine together in a friendly atmosphere can't get any better than that). Thank you for your help with our family Legoland travel (we will be visiting Legoland on a Saturday! I have printed out the timetable from the link you provided, just in case, my WIFI isn't working at that location.
We have decided to stay in Esslingen at the HOTEL AM SCHELZTOR as it is near the train station and a bus stop.
Do you have any suggestions for restaurants, shopping, sightseeing in Esslingen?
We are looking forward to visiting this part of Germany as we have never been there in our past travels.

Esslingen is a great place to stay when visiting the region, just be sure to note that on weekends the S-Bahn (the train into Stuttgart) only runs every 30 minutes or so. That hotel is a good location between the train station and the old city.

Much of the attraction in Esslingen is soaking up the atmosphere, but don't neglect to go inside it's churches, particularly the stadtkirche St. Dionys. On Wednesdays and Sundays there are public guided tours (in German) to the crypt of the church to see early construction from the 700s! It's very cool. You can book private tours in English by calling or writing the city museum in advance if you'd like to actually understand what you're looking at down there! The city museum, housed in an 700 year old merchant's mansion, has some neat exhibits but is entirely in German as well.

Going up the "Burg" - a fortress, not a castle - is a must. My secret is go up the winding path in the vineyards, and go down the covered staircase. The stairs feel never ending and the walk up the road isn't actually that bad. Once up there the views are amazing and there's a large park behind it.

My in-laws like the J.F. Scrieber museum - also in a historically significant building - which focuses on historic paper dolls and models.

Be sure and visit the Kessler Sekt cellars (also in a - guess what - historically significant 800 year old building!). This is Germany's first sparkling wine cellar, using techniques brought back from Champagne by Georg Kessler in the 19th century. This is the festive drink of German state dinners, but the prices are surprisingly reasonable. You can try some at their shop, the people who work there speak good English and if not too busy can describe the different varietals.

For food, Weinkeller Einhorn is THE place in town for traditional Swabian food in a lovely setting. Reservations are a good idea, though. If you get sick of German food, Copper Bowl serves authentic and delicious South Indian food on the Marktplatz (if you want to sit inside, reservations are also necessary, as it's small. Plenty of room outside though.) L'Osteria has good wood-oven pizzas and pasta dishes, large portions for price, in an amazing setting on an island in the river. Galleria Zeus has slightly upscale Greek food and great hospitality. For fast food, Konuk Kebap is one of those kebap shops that use real meat with texture and flavor.

It's funny, I'm literally just about to head over to Esslingen to negotiate getting a group of 22 tourists into a traditional tavern for some wine. My reward for this is lunch at Copper Bowl. I hope you enjoy Esslingen as much as I do!