30th anniversary. Within half hour of Acton.
Here are some choices: ( sorry not entirely sure about entertainment, but the food is good and they are all near by)
-Monument Grill in Leominster
-J's restaurant @ Nashoba Valley Winery
-Alcotts Restaurant & Tea Room in Harvard
-Cast Iron Kitchen in Maynard
-Chloe American Bistro in Hudson
-Walden Grill in Concord
-Allora Ristorante in Marlborough
-Coral Seafood in Marlborough
How about AKA Bistro in Lincoln? Great reviews and Sushi + French can't be that bad.
The atmosphere at J's at Nashoba is great for a special occasion.
Edit, sorry, missed the part about entertainment. I think Chloe has Jazz nights.
145 Lincoln Rd, Lincoln, MA 01773
Been to both AKA and Gibbett Hill...both good, not great...AKA is OK...a little busy...but good if you want french and sashimi...Gibbett Hill is good for a mid-upper priced steakhouse...full bar....AKA has beer and wine...
How about the Stonehedge Inn in Tyngsboro...definitely a cut above for an anniversary...
160 Pawtucket Blvd., Tyngsboro, MA 01879