My husband and I are considering going to Portsmouth, NH around Labor Day. We have never been to New England. We are flying from Chicago for 4 nights and wanted somewhere that would be easy to get to. We were told it was a quaint New England town. We would love to drive along the coast if it is worth it (we love driving the coast in California). Would there be enough to do for 4 nights? What other towns should we visit that are close? We don't think we want to go into Boston or anything like that. How is the weather early September? Any hotel suggestions? Thanks for any advice!

Portsmouth still has a working waterfront butis also strong in arts and history. The historic Strawbery Banke area has preserved some beautiful homes and gives visitors an idea of what Portsmouth was like. There are a variety of restaurants in all price ranges, a couple of theaters, and music venues. You can take a harbor cruise, visit the Isle of Shoals, or take an inland rivers cruise. The dock is within walking distance of the parking garage. There's a small downtown area with interesting and unique shops. You can head further south on the coast with a lovely drive thru Newcastle and past the renovated historic Wentworth-by-the-Sea hotel. Another nice drive is along the ocean for a look at the mansions except, unlike Newport, these are private. Or head north, over the bridge to Kittery ME with both outlets malls and backroads to explore. Portland ME is also an option. I haven't been to the CA coast so I suspect there is a lot less coast to look at (NH only has 17 or 18 miles of coastline). The weather on Labor Day weekend is usually wonderful. It can still be very warm but with cool nights. From Portsmouth you could also make a day trip to the White Mountains or head south to visit places like Newburyport, Gloucester. If you like antique shops, go west toward Concord via Rt 4 and "Antique Alley" in Northwood. You could also do a loop that includes a visit to Flag Hill Winery and Distillery in Lee NH.

I believe there is plenty to do in the vicinity of Portsmouth to spend 4 nights. I would recommend that you stay at the Wentworth by the Sea - its a Marriott and a lovely old property that was recently renovated. Its actually in New Castle, NH but its adjacent to Portsmouth. New Castle is very quaint and scenic. The hotel is also right on the water.

In the Portsmouth area, you can shop in Kittery Maine where there are tons of outlets. You can tour Stawberry Banke and see lots of historical homes. You can take a hike through Ordione State Park in Rye and see the rocky shore of NE and several lighthouses. You can drive along Rt 1a through Rye and see the ocean and lots of pretty homes. You can take a short drive up to York ME and see more rocky shore and a beautiful lighthouse. You can drive a few hours and get up to the White Mountains of NH.
There are several very good restaurants in Portsmouth so you won't go hungry.

Portsmouth is terrific. Also within an hour's drive are Kennebunkport and Ogunquit in Maine and Newburyport, Rockport and Salem in Massachusetts (to name a few) - all unique and beautiful seaside towns.

Portsmouth is very nice but I think 4 nights might be too much. I would suggest you divide your time to have two nights in Portsmouth and two nights in Portland Maine. Portland is a great little city with lots of history and water front. Staying Portland would also give you the opportunity to explore a little more of the Maine coast which is beautiful. In any case, labor day and Sept are perfect in terms of weather. Enjoy.

Everyone's suggestions are good. If you do go to Kittery, bring your own wine or beer and go to the Lobster pond on Chauncy creek. Down a ramp and sit at wooden tables beside the creek. Be aware, our coastline is nowhere
as beautiful as California to drive for ocean views.

Thanks for the advice! Does anyone have input on the Port Inn?

The Port Inn isn't in a great location. It's on the traffic circle which isn't a bad area but certainly not within walking distance of downtown.

I'd stay downtown where you can walk to the harbor, shops, restaurants, Strawbery Banke, etc. Try the Sise Inn, Bow Street Inn or the Sheraton Portsmouth. Wentworth by the Sea in New Castle is also a great option.